


An Actual Stroke of Winchester Luck

by Superwho_Scribblings (PrepareToBeMildlyEntertained)



Series: Henry Verse [1]
Category: Supernatural
Genre: Angst, Bunker, Canon Divergent, Case, Drama, Established Relationship, Family, M/M, Men of Letters, Men of Letters Headquarters, Season 8, Season/Series 08, supernatural books
Language: English
Status: Completed
Published: 2013-11-12
Updated: 2013-12-02
Packaged: 2018-01-01 08:14:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 24,452
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1042473
Author URL: https://archiveofourown.org/users/PrepareToBeMildlyEntertained/pseuds/Superwho_Scribblings
Summary: <blockquote class="userstuff">
              <p>What if Henry Winchester never had to die? Henry makes it through his encounter with Abaddon and comes to live in the bunker with Dean and Sam, learning more about their lives, their friends, and even angels?</p><p> Canon-divergent from the end of As Time Goes By, plus I twist some other stuff around from the beginning of Season 8.</p>
            </blockquote>





	1. What's One More Weary Head?

**Author's Note:**

> I feel like I don't see enough fanfiction with Henry, so here we are. This whole section will mainly be retelling season 8, so be ready. Also, there won't be much Destiel until later. This chapter will only have mentions. I have a ton more written and will be updating regularly. Please enjoy and leave comments!
> 
> Oh, and please follow me on tumblr: http://preparetobemildlyentertained.tumblr.com/

          Henry’s breathing was shallow as Sam held him. The blood was seeping out the side of his mouth at a dangerous rate, but he was fighting to hold Dean’s eyes.

          “We did it,” he sputtered out. Dean looked at him sadly.

          "No, _you_ did it,” he said, “For a bookworm, that wasn’t bad, Henry.” Henry smiled slightly and coughed a bit more, groaning.

           “I’m sorry I judged you two so harshly for being hunters,” he said, “I should have known better.” Sam looked curiously down at him.

           “About?”

           “You’re also Winchesters. As long as we’re alive, there’s always hope. I didn’t know my son as a man, but having met you two,” Henry reached out and grasped Dean’s hand firmly. The grip was tight enough to cut off some circulation, but Dean didn’t pull away. “I know I would have been proud of him.”

            Henry’s eyes fell closed and Dean sucked in a sharp breath. Someone else gone. Another member of the family dead. Just another Winchester grave to dig. He fell back from his crouched position to the floor, sitting roughly. He looked utterly lost. Sam still held Henry’s body firmly.

            “Dean,” came Sam’s voice suddenly, “Dean, he’s still breathing.”

            Dean was up in a flash and had his hand to Henry’s throat for a pulse before Sam could blink. There. It was weak, but still there. Not dead yet.

            “Hospital.” Dean said, without looking at Sam. He ripped off his shirt and pushed it against the deep wound in Henry’s stomach. He gestured to Sam to let Henry’s body down to the ground. With his bleeding grandfather (that was never going to not sound weird) out of his arms, Sam ran to the Impala out front and returned quickly with a roll of duct tape. The sharp sound of the tape being pulled off of its spool filled the warehouse for seconds while Sam got a strip long enough to wrap around Henry’s body a couple of times to keep Dean’s shirt in place over the bloody stomach.

            The boys didn’t have to say anything to each other as they went to either side of Henry and lifted him as gingerly as possible. At the car, Dean dropped the arm he was holding to rip open one of the back doors and then help his brother into backseat with Henry. He checked his weak pulse again before he ran around to get into the driver’s seat and pulled quickly onto the road.

            “How is he?” Dean asked, keeping his eyes on the rearview mirror more than the empty road in front of him.

            “Alive.” Sam replied tersely. “Sort of.” Sam had enough experience with injuries to know this wound was bad. Really bad.

            “The hospital is five minutes away,” Dean said, pushing down the gas pedal even harder. They were now pushing 90 MPH, but Dean wasn’t worried about cops. He wasn’t even thinking of getting pulled over as a possibility.

            They got to the hospital, normally a fifteen minute drive, in just over four minutes. The nurses in the ER heard the loud motor pull up outside and then a loud, deep voice shouting, “we need some help out here!”

 

* * *

 

 

            Henry was alive. That was all that mattered, currently. Dean had gone back to the warehouse as soon as Henry and Sam were inside the hospital to finish cutting up Abaddon. No way would she be bothering them again.

            When he got back to the hospital, Sam was pacing in the waiting room. Henry was in surgery. Dean took a day to create enough fake documentation to prove that Henry was their brother so that they would actually be allowed into his hospital room. Dean had started laughing in the middle of creating the documents when he thought about what would happen if he tried to tell the hospital how Henry was _actually_ related to them.

            Now, though, Sam and Dean were at the bunker. Halfway through the first week of Henry’s recovery, the brothers had finally decided to go and see if it was even still standing. The bunker had much more to offer, though, than just its continued existence.

            Dean loved his own room and his own space, and Sam’s face (Dean wished he could have taken a picture) had lit up like Christmas morning upon seeing the frankly ridiculous number of books the place had. Their second day at the bunker, Dean had walked in on Sam just lovingly stroking a finger along the spines of all the books. _That_ Dean had gotten a picture of.

            Henry continued to not die, which was nice. Dean had been the one in the hospital room the first time he woke up. He was on Sam’s computer looking for a hunt nearby when he heard the hospital bed shift and saw Henry open his eyes.

            “Henry?” Dean asked, standing up and moving towards the bed. Henry blinked a few times and started looking around in wonder and confusion until his eyes landed on Dean, now standing a couple feet away from the bed.

            “Dean,” he looked around again, “what happened?”

            “Well,” Dean put one of his hands in his pocket, “Abaddon did her best to kill you. But, like I said, you’re tough for a book worm. You’re in the hospital. You’ve been out for five days.” Dean clamped his mouth shut before he really started yammering. Henry went to sit up and Dean moved forward quickly, putting his hand on his grandfather’s shoulder.

            “Yeah, let’s take that slow,” Dean said, meeting Henry’s eyes. “You only barely made it. It’s going to take you some time to heal up.” Henry clenched his jaw and nodded, then his eyes widened like he just realized something. The heart monitor near the bed started beeping faster.

            “Where is Sam?” He looked around frantically. Dean put his hand against Henry’s shoulder more firmly.

            “Sam is fine. He’s at the bunker, doing some research.” Henry’s agitation went down and he relaxed his muscles. Dean removed his hand and held both in the air as if to ask ‘we ok now?’ before Henry processed what Dean had said.

            “The bunker?” he asked, “it is still standing?”

            “Yeah!” Dean said, face breaking into what Sam would call a wide smile, but what Henry only recognized as a slight lift at either side of Dean’s mouth, “You’ve seen it?”

            “No, I hadn’t been fully initiated yet.” Henry said. Dean nodded.

            “Well, it’s awesome. You’re gonna love it.” Henry’s eye twitched in confusion at Dean’s use of the word ‘awesome’ but he didn’t say anything. He jumped a bit when a guitar riff seemed to blast out of Dean’s pocket. Dean help up a finger and pulled out what Henry now recognized as his phone.

            “Yeah, Sammy?” Dean answered. He turned away from Henry. “Where at? Yeah, yeah. We should check it out. Hmm? Oh, he’s awake! Doc’s saying he’ll do fine. Lucky, yeah. See you then. Yeah, bye.” He pulled the phone away from his ear and put it back into his pocket.

            “So I’m lucky, then?” Henry asked. He didn’t sound like he felt lucky. Dean looked at him with a distinctive ‘suck it up’ face.

            “Yeah, you’re lucky; you’re still sucking in air.” Dean said, and then looked at the oxygen tubes going into Henry’s nose. “Kinda.” Henry felt a muscle in his jaw twitch but he didn’t argue.

            “Sam found a job for us,” Dean said, finally. “We have to go take care of it. Will you be cool with us being gone for a couple of days?” Henry screwed up his jaw even more in annoyance.

            “Dean, I am not a child. I can be left alone, thank you.” Dean smiled a bit.

            “Oh, by the way, they, uh, think you are mine and Sam’s brother here.” Dean said, moving towards the door. “Didn’t think they’d buy the ‘he’s my time-traveling grandpa’ story.” Henry took the information in with a nod of his head.

            “Oh!” Dean said again, and moved back towards Henry. “Almost forgot, I got you a phone.” He handed Henry a cheap, disposable phone which Henry just looked slightly confused by. Dean quickly showed him how to find and call either him or Sam and, just in case, a hunter named Garth who Dean said would help if anything happened. Dean didn’t elaborate.

            And then he was gone and Henry was alone in the pristine room. Nurses bustled along the hallways outside quickly, some coming in every now and then to check on him. Henry just focused on trying to get better and waiting for his grandsons to come back.

 

* * *

 

 

            A couple of weeks later, Henry got out of the hospital and drove back to the bunker with Dean and Sam. He sat silently and listened to the brothers talk.

            “Are you honestly telling me you _weren’t_ super-obviously checking that doctor out?” Sam said, smiling. Dean scowled.

            “Dude, what the hell? No, I wasn’t.” He didn’t look at Sam. “Why the hell would I have been checking him out?”

            “Well,” Sam said, and Henry noticed the sly smile that slunk its way across his lips, “I thought maybe his was another one of your ‘gay things’”. Dean swerved the car in surprise. Henry could understand the shock. Unless this was a normal topic of conversation?

            “I told you that wasn’t what it sounded like.” Dean said, through gritted teeth.

            “I don’t know,” Sam said, “I just thought you belonged to someone else.” Dean grumbled but didn’t dispute Sam’s claim.

            “Bitch.”

            “Jerk,” Sam responded easily.

Henry stayed quiet. He got the feeling that this was how the brothers almost always interacted. Light bickering and teasing. And then, he assumed, huge emotional blowouts.

            “So, Henry,” Dean said, glancing at his in the rearview mirror, “how about I introduce you to some music a bit ahead of your time?” Now Sam rolled his eyes and turned to look out the window.

            “I would be interested in that, yes.” Henry answered carefully. He had always enjoyed music. He did have an interest in how music had evolved since his time. Dean grinned at Sam as he shoved a black tape into the dashboard of the car. Henry jumped at the sound of loud guitars pumping through the speakers. Sam winced at him in the mirror sympathetically. The music was loud and… hard, Henry decided. He shifted uncomfortably, but looked at Dean in the front seat, who was smiling and hitting the steering wheel in time. He sang loudly and off-key at the chorus.

            “You shook me aallll niiight long,” Dean belted.

            Henry noticed Sam looking annoyed, but he could see by the twitch in Sam’s mouth that he really did enjoy it. Henry decided he liked this side of Dean too. He tried to let himself enjoy the music and found, after about an hour, that he really did. He liked the rough tones, and the way it brought out a gentler side of Dean. He did finally find his voice.

            “What was the job you went on while I was still at the hospital?” Dean turned down the music, but he didn’t look annoyed at the interruption.

            “Oh, we didn’t tell you?” He asked, sounding surprised, “it was a Golem!” Henry’s eyes widened.

            “Really? A Golem?” He had only read about them a couple of times. He shifted a bit when he remembered what exactly his grandsons did for a living. “Did you kill it?”

            “What?” Dean asked, looking hurt for a split second before hiding it. “No, we didn’t kill it. We don’t just _kill_ everything.”

            “Well,” Sam started. He was silenced by a particularly nasty look from Dean.

            “We just helped the guy he belonged to get control of him,” Dean said, “and, well, killed a couple of the guys who were trying to use him for less than awesome reasons.” Sam had never heard Dean being uncomfortable admitting he killed someone. Henry looked at Dean and then looked back down nodding.

            “I’m sorry I assumed,” he said. Dean waved his hand.

            “Don’t worry about it.” The car was silent for a while. Finally, they began pulling up the dirt road that led to the bunker, when a question that had been bothering Henry finally couldn’t be held in any longer.

            “Do you mind if I ask,” he began, swallowing thickly, “how John died?” Sam’s eyes widened and he glanced at Dean, who stopped the car sharply in front of the door to the bunker and got out quickly without saying anything. Henry’s gut turned over but he didn’t retract his question.

            “Dean… doesn’t talk about it.” Sam said.

            “I gathered.”

            “It has been years, but he hasn’t ever really dealt with it.” Sam didn’t look back at Henry. “Dad sold his soul for Dean after we got in a crash a few years ago. His life for Dean’s. We didn’t find out until later. I was… Dean woke up. Dad took his place.” Sam looked back at Henry when he didn’t say anything.

            “Look,” Sam said, “I may not have gotten along with my dad. You probably already know that from reading his journal, but he cared about us. He cared about Dean. And Dean doesn’t like to deal with that kind of thing.”

            “Thank you for telling me,” Henry said, quietly. “I think I understand now.” Sam nodded.

            “Now, you probably shouldn’t even be out of the hospital to begin with, but you especially shouldn’t be sitting in an ancient, uh, I mean, _any_ car for this long.” Sam said, opening his passenger door and then going back to open Henry’s. “Let’s get you inside and I’ll get you all set up in your room.”

 

* * *

 

 

            Time went by slowly for Henry at the bunker. Dean and Sam didn’t let him do much of anything, and they _never_ let him leave. It was as if they were somehow concerned that if people saw him they would somehow immediately know he was a time traveler or something, which made absolutely no sense. But there was still plenty to keep him entertained while he was stuck, stuff from his time. All of the records of the Men of Letters were fascinating, and there never seemed to be an end to them. Henry shared his excitement to learn with Sam, and they could often be found reading the books in the bunker late into the night together.

            Now that Sam had taken on the duties of the Men of Letters, he was particularly interested in learning from Henry. They were at the table one evening when Dean walked in, carrying three plates precariously on his arms. He set two of the plates down in front of Sam and Henry and then retreated back to his own seat. Sam looked up from the book he was flipping through.

            “You made these?” He asked incredulously, indicating the cheeseburgers.

            “We have a real kitchen now,” Dean said. Henry picked up his burger without saying anything and looked at it once before he put it into his mouth.

            “Yeah, I just didn’t think you knew what a kitchen was,” Henry heard Sam respond, but he didn’t hear what was said after that. He made a noise he would completely deny later as the flavors of the burger swirled around in his mouth. Dean looked at him and smiled, then turned to Sam expectantly. Finally Sam picked up the thing and took a bite.

            “Wow,” Sam practically whistled. The burger was perfection. The meat was cooked exactly right, and he didn’t think he’d ever tasted a cheese like this, but it went along with the flavor of the burger exactly. Dean preened like a peacock and went to take his own bite when his phone went off in his pocket. Sam didn’t even notice, but Henry looked up to watch Dean on the phone.

            “Kevin?” Dean asked, talking loudly into the phone. Sam looked up in recognition of the name, but Henry didn’t recognize it. Dean hung up with a click of a button, looking annoyed, but Henry could also see the worry.

            “Is something wrong?” Sam asked, not putting his burger down.

            “Guess,” Dean stood up from the table, grabbing his burger. No way was he leaving that behind. They both started to move towards the bunker doors when Henry cleared his throat.

            “I suppose I am staying here?” He asked, setting up his face to look as annoyed as he felt at being forgotten. Sam turned around apologetically.

            “Oh, yeah, sorry Henry,” he said, “with you still healing up and all…”

            “We have to go check on a friend,” Dean said, leaving the room. Sam looked after him with the beginnings of a particularly impressive bitchface. Henry shifted in his seat.

            “I only wish I could be useful.” Henry said, not looking away from Sam.

            “You are useful,” Sam said, “Dean just doesn’t know that yet. He is really slow to trust but don’t worry. He’ll get there. We _do_ have to go check on a friend, though. But we’ll, uh, be back in about a day. There’s plenty of food in the fridge, so you should be fine, right?” Henry knew that not taking him along was due to his injury, and not the fact that the brothers didn’t want him around, but he still wasn’t pleased. He eventually nodded and listened as the brothers made their way up and outside, finally hearing the slam of the bunker door.

 

* * *

 

 

            Ever since that job that had started with a phone call from Kevin, Henry had known something was off with Sam. They had come back to the bunker later that night, and then left for a week before returning, covered in some kind of black ooze. Sam told him about the trials and exactly how Dean felt about them. Henry couldn’t even be mad at Dean for letting Sam do the trials because he knew, if he had had his way, neither one of the boys would have been attempting them. And now Sam was trying to cover up the fact that he was coughing up blood. The first time Henry had noticed, Dean was in the room, and based on the way Sam was being so secretive, Henry didn’t say anything until Dean left.

            “Sam,” Henry turned to him as soon as the older Winchester was gone, “why aren’t you telling Dean?” Sam tried to blow it off.

            “Tell him what?” He sniffed and tried so look confused but instead he ended up coughing. A lot. More blood went into a nearby tissue. Henry looked at it pointedly and then back at Sam.

            “Sam, if you can tell me why you won’t include Dean and I agree, I won’t tell him.” Henry said, “But he deserves to know. You should not keep this from him.” Sam bit his lip and looked at the doorway Dean had just passed through before answering.

            “Look, Dean can’t know because he thinks he should be the one who is going through this. He is already pissed enough at me for taking over, and that’s before he finds out. I’ll tell him just… not yet.” He looked at Henry pleadingly.

            “Hey, you girls want some dinner?” Dean called from the other room.

            “Of course,” Henry called back, not taking his eyes off of Sam. He stood up eventually, and started moving towards the kitchen. As he passed the table, he picked up Sam’s bloody tissue and tossed it in a nearby garbage can. He looked at Sam while he did it. Then he walked through the same door Dean had walked through a few minutes earlier without saying another word.

 

            A week later, Henry was interrupted from his cataloging by the loud noise of the Impala pulling up outside. The boys had been gone for a long time. Before long, he heard their voices echoing through the bunker.

            “So, what really happened with Cas?” Sam’s voice said. Henry scrunched his eyebrows together. He had heard the name Cas before, but never more than a mention, and really only by Sam.

            “I don’t know,” Dean sounded tired, beaten, and overall completely destroyed. Henry had never heard him sound like this. “Naomi… she’s had control since we got out of purgatory. Mind control.”

            “Angel mind control? Really?” Sam sounded incredulous, Henry just focused on the words ‘angel’ and ‘purgatory’. He had known that Dean had been gone for a year, but had never known where. Had he been in purgatory? And did angels actually exist?

            “All I know is I can’t take any more lies. From anyone.” Henry heard the voices getting closer, but he didn’t move. He swallowed as he realized what Dean meant. Based on the silence, Sam had figured it out too. Before Sam could respond, they entered the room Henry was in. He hadn’t moved yet and was looking at Dean warily. He looked just as wrecked as his voice sounded. Henry’s eyes widened in shock. What could have happened that would leave him looking like that?

            “I’m sorry, Dean,” Sam finally said, looking down.

            “I was going to make him tell you,” Henry said. Sam looked up at him in fear, shaking his head, but apparently the worst was already done.

            “Wait, you _knew?_ ” Dean asked, eyes flaring up angrily as he took a few steps closer to Henry, who suddenly figured out just what exactly he had done wrong.

            “Honestly, it was hard not to notice,” Henry said, standing up. He was done taking so much abuse from Dean. “If you spend more than a few minutes with him he is coughing up blood, but you are so determined to stay away from me that you seem to be oblivious to it!” Dean was seething and Sam looked terrified as his eyes flicked back and forth between his brother and his grandfather.

            “Are you telling me I don’t care about Sam?” Dean asked, practically growling.

            “Of course not!” Henry shouted, rolling his eyes, which just puffed Dean up even more. “You care about him more than is likely healthy, but you can’t get over your hatred of me.”

            “Maybe I would trust you if you actually told me the truth!” came Dean’s response, but Henry had had enough. He took the last few steps forward until he was right in Dean’s face, both of them breathing hard.

            “No, no you wouldn’t. You refuse to trust me because you still hold resentment for me leaving John, even though you know as well as I that I can’t change what I did. You blame me. You blame me for losing your mother, for living the way you do, and you blame me for your father’s death too.” Dean looked taken aback by the sudden speech, and couldn’t find his own tongue before Henry continued. “But here’s the thing, Dean. I already blame myself for John’s death. I blame myself every day. It is crushing me down because I know that I am the reason my son died the way he did, and yet I can’t find it in myself to be angry, because I am proud of him. I am proud of him for dying, because it meant saving you, and I know from experience that saving a son is much better than losing one.” With that, Henry turned on his heel and marched out the door and down the hallway to his room.

            Dean and Sam heard his door slam and they stood there in shocked silence for a while. Dean’s eyes, already broken from the encounter with Cas, now looked like smashed shards of green glass. Sam made a mental note to find the majority of the alcohol in the bunker and hide it tonight.

            Still silent, Dean clenched his fists tight and the unclenched them before turning and walking down the hallway to his room. Sam was left alone in the silent room. He was about to walk to his bedroom when he started coughing. Hard. He stumbled a couple of steps to the table where he grabbed a tissue to put to his mouth. He put his whole weight against the table as the coughs wracked his body. When he finally stopped, the tissue was full of blood. He exhaled heavily, head falling down.

            “Here,” Henry’s voice shocked him so much he nearly whacked the cup of water out of his grandfather’s hand. Henry smiled slightly. “Sorry to startle you.” Sam took the cup gratefully and took a drink.

            “Thanks,” he said. “And sorry. About Dean.” Henry pushed his hands into the dark jeans he was wearing. They had taken him shopping shortly after he arrived at the bunker, but Henry still felt uncomfortable in some of the clothes. He never really dressed as casually as Sam and Dean did. He never wore T-shirts, especially the screen-printed band shirts that Dean had a huge number of. For the most part he wore dark wash jeans and button down shirts, though he left them untucked. Currently he was wearing a baby blue shirt that looked wrinkled, like he had possibly slept on it the night before.

            It seemed unusual for Henry to sleep in his clothes. He never did, as far as Sam had observed. He was always very serious about looking nice each day, despite the fact that he saw no one besides the brothers. Sam took notice of the wrinkled thing.

            “Henry, did you sleep in that?” He asked, indicating the shirt. Henry looked embarrassed as he looked down and fingered the hem.

            “I, uh, couldn’t sleep last night,” Henry said, not looking up. He reached up and scratched his chin, which Sam now noticed had not been shaved that day. “I was worried.” He said it so quietly that Sam almost didn’t hear him. Sam looked at him curiously.

            “You were worried? About us?” He asked. Henry nodded.

            “Of course I was worried. You are my grandsons, after all.” Sam made a noise in the back of his throat that sounded like surprise.

            “I’m sorry that we worried you.” Sam said, honestly. He hadn’t even thought of Henry being concerned about them. At this point, he wasn’t used to anyone possibly worrying about them. It had been just him and Dean for so long now. The room was quiet for a while. Dean never came back out of his room. Sam had a pretty good idea why but he wondered if perhaps he should let Henry in on why his mood was as foul as it was.

            “Henry,” Sam started, “he isn’t just mad at you and me tonight.” He started, unsure of how much to tell Henry at this point. He had started wondering a few days ago just when they would approach the subject of Cas. Apparently the time was now.

            “Why else is he upset? Something about someone named Cas, from what I heard.” Sam nodded in affirmation.

            “Castiel is his real name. He’s, um, an angel.” Sam looked to Henry to see his reaction. His eyebrows were pulled together.

            “An angel?” He asked, but not in a disbelieving tone, just one of clarification.

            “Yeah, an angel.” Sam was glad he wasn’t going to have to try and prove to Henry that angels did, in fact, exist. “He and Dean are close. Really close. And we sort of lost Cas today. In a way.” Sam said. He wasn’t explaining this correctly at all. Then again, he thought he was doing a better job than Dean would have. Or Cas, for that matter.

            “Close? As in, they were friends? But are you not friends with him?” Henry asked. He looked like he was trying to understand, but Sam knew he was missing pieces of the story. He sighed and finally decided that Henry was going to need the whole deal.

            “Close as in… romantically.” Sam shuddered using the word. It wasn’t the right thing to describe Dean and Cas. They weren’t some lovey-dovey couple. They made each other better and stronger. He could play at being grossed out by their extended relationship, but he knew they were happy. Happier than Dean had been in as long as he could remember. Henry’s eyes widened more than Sam thought was physically possible and Sam suddenly recalled the fact that Henry was from a very, very different time.

            “Romantically?” Henry choked on the word a bit.

            “It’s actually pretty common now,” Sam said, trying to figure out how to explain fifty years of evolved social norms in a way that Henry could understand. “Men and men. I mean, there are debates and stuff. But, I mean, the thing is, Cas isn’t even technically a man. I mean, he looks like a man, but angels are genderless!” If anything Henry looked more confused and Sam made a frustrated noise. He looked down.

            “I have never seen Dean happier than when he is with Cas,” Sam said, as a last resort. It was all he could do to explain now. Henry hadn’t seen them together. He had never been exposed to that lighter side of Dean, that side that only came out when Cas was around.

            “Dean is _romantically involved_ with an _angel_?” Henry asked. He sat down halfway through his question in a chair nearby. At least he didn’t comment on the fact that the angel was a man, Sam thought.

            “It happened while Dean and Cas were stuck in Purgatory,” Sam said, then thought back. “Did you know that Dean was in purgatory?” Henry shook his head. He looked overwhelmed, which Sam thought was to be expected. He told Henry about the rest of the events with Cas that day in terms as simple as possible, and at the end, Henry actually looked like he was grateful to understand a bit more.

            “So, he _is_ angry at me, but not all at me,” Henry said. It wasn’t a question. “He lost someone close to him. Was hurt by someone he cared about deeply.” Sam’s coughing cut off any further conversation. His body shook as he coughed and coughed into a tissue and before too long, Henry had tentatively walked forward and put a hand on Sam’s shoulder. The strength there was reassuring and Sam found himself unduly grateful for it.

            “You should rest,” Henry said once Sam had stopped and another tissue was thrown in the trash. Henry’s hand still rested on Sam’s shoulder but he reached the other hand out to Sam to help pull him back up to a full standing position. Henry helped Sam out of the room and down the hallway, almost falling over at the huge weight Sam put on him with his body. He was nowhere near Sam’s size and was struggling. He eventually got his youngest grandson into bed and he wiped his forehead in exhaustion.

            He looked at Sam’s sleeping form with tenderness. He really did love both of the brothers. They were his grandchildren, his blood, and he found he couldn’t help but worry about them when they were hunting, though he knew they could take care of themselves. Sam’s sickness was worrying him even more, and now he had Dean to worry about. Dean and Cas. He couldn’t quite process the whole idea of it, but the way Sam spoke about them, he found he didn’t find it disturbing. He was just upset that Dean had been hurt so badly. He knew what it felt like to be ripped away from someone you cared about.

            “Sleep well, Sam,” Henry said, looking at him once more before leaving the room and closing the door behind him. He walked down the hall silently into his own room and fell asleep instantly. He didn’t even notice Dean, standing just outside where Henry and Sam had been talking, still looking broken, but maybe a little better than before.


	2. Sunny Days Aren't Here Just Yet

**Summary for the Chapter:**

> Sam is getting more and more sick, Dean is still treating Henry like a house guest, and apparently someone named Carver Edlund wrote some books called Supernatural? And when was anyone going to mention that both Henry's grandsons had been to hell?

**Notes for the Chapter:**

> I'm so excited to publish this section. Writing Charlie was my favorite part of writing this first section of the Henry verse, as I adore her. Still no appearances from Castiel, but it should be coming up in the next chapter. Enjoy!

 

            “Why are you letting him hunt?” Henry was yelling again. He and Dean still yelled a lot, much to Sam’s disappointment. But this time Sam was mad for an entirely different reason.

            “You two don’t get to decide what I do, I’m a grown man,” Sam growled from his chair a few feet away from the argument. Dean ignored him.

            “I have _tried_ to keep him inside, but if I leave without him, he will just go out anyway!”

            “I am _right here,”_ Sam said. He was still ignored.

            “I could keep an eye on him,” Henry said, trying to reason with Dean. “But you know he shouldn’t be out in the state he is in. You could get him killed if you let him leave like this!” Sam groaned.

            “You saying it would be my fault if he died?” Dean asked in acid tones.

            “Obviously not!” Henry tried to backpedal, “I’m saying that you need to protect him and you aren’t right now.” Sam had to hand it to Henry, it was pretty clear how much he cared, but Dean wasn’t having it.

            “Look, I’ve tried to talk to him. I’ve explained all of this. But here’s the thing: _you don’t know him._ ” Dean pointed a hard finger at Henry’s chest. “I do. And right now, he is going to just keep fighting until I let him leave this fucking bunker. Got it? Come on, Sammy.” Henry looked like he was about to say more when Sam was suddenly right in front of him.

            “I’m going, Henry,” he said, words laced with iron. Henry exhaled roughly and looked down, defeated.

            “Fine, do whatever the hell you want,” he said, walking away sullenly. “Glad to see that you have about as much of a need for self-preservation as your brother, Sam.” Dean was in the other room, and must have heard, but he didn’t say anything. Sam had already had this fight with him. He glared at Henry for a few moments before he turned to leave.

            “We’ll call, Henry,” he said, stopping in the doorway. “We’ll both be fine.” And with that he left, leaving Henry sitting alone at the huge table, head hung in defeat.

 

* * *

 

 

            They did come back, as promised. They didn’t talk about it much. It was something to do with an old friend named Krissy and revenge on some vampires. Henry wasn’t talking to Dean, Dean wasn’t talking to Henry. Sam just wanted everyone to stop treating him like a 5-year-old. When the brothers had said they were going to meet with their prophet friend, Kevin, again, Henry had stayed totally silent, not even moving until he heard the Impala drive away. After he knew they were gone, he picked up one of the huge volumes from the table and threw it across the room, knocking over a lamp. The bulb shattered loudly.

            Hours later, the boys finally called. Henry understood the mechanics of a cell phone now. Not how it actually worked, but he got the most important bits. Hit the green button to answer the phone, hit the red to hang up and it didn’t matter where you stood, you could talk to the person on the other end of the line. He hit the green button with force.

            “Sam?” he answered. Dean never called him.

            “Hey, Henry,” Sam sounded wound up and worried. “Kevin, he uh, told us what the second trial is.” Henry stood up from the table and started pacing.

            “What?”

            “Rescue an innocent soul from hell and release it unto heaven,” Sam said. Henry heard the distinct sounds of the Impala in the background of the call.

            “And you know how to do that?” Henry asked, running one hand through his hair nervously.

            “Well, no,” Sam answered honestly, “but we are going to find someone who does.” He didn’t elaborate, but he didn’t have to. Henry stopped and slowly rolled his eyes up towards the ceiling. Were they really that stupid?

            “A crossroads demon?” Henry asked, hoping he was wrong. The silence on the other end of the line sort of shot that hope in the ass. “You are going to summon a crossroads demon?”

            “To be fair, we’ve both done it a few times before,” Sam said. Henry just gripped the little phone more tightly to his palm.

            “You have,” he said. He hadn’t known about this before. One of these days he was going to make both of them sit down and tell him everything. He constantly felt out of the loop.

            “Yeah, we have.” Sam said. The sounds of the Impala were cut off and Henry knew they were where they had been headed. “Look, we’ll be fine, Henry. No big deal. We’ll talk later.” And with that, Sam hung up, leaving Henry talking into empty air.

            “You better.”

 

* * *

 

 

            The boys didn’t call. And didn’t call. When Henry finally went through the steps that Dean had shown him to actually place a call, a voice at the other end informed him that the cell was not in an area of service. Eventually, Henry even called Dean, but he didn’t answer either. The bunker went from an absolute mess, due to Henry’s fits, throwing things around and generally being destructive, to spotless, as a result of Henry’s need to be doing _something,_ even if that something was cleaning _._ The next day, his phone lit up and light piano music started playing. Henry was surprised to see Dean’s name on the small screen.

            “Dean, where the hell have you been?” He demanded as soon as he had pressed down the green button.

            “Henry, I’m sorry,” Dean started. Henry shut his mouth. Dean never apologized.

            “What happened?” he asked more softly now.

            “Sam and I, we found a way to… get into hell, right?” Henry nodded, even though Dean couldn’t see him. “Well, I was looking for Kevin and,” Dean gulped loudly into the phone. Henry was trying not to be impatient.

            “Dean, come on, what happened?” He urged.

            “Naomi,” Henry searched his mind for the name before he remembered the conversation that felt like it had been years ago. The one who had brainwashed Cas. Henry sat down heavily in a chair. This wasn’t going to be good. “The bitch came and tried to get me on her side. But when I told her no, she finally told me exactly _how_ Sam got himself into hell. He went through purgatory, Henry. Fucking _purgatory_.” Henry suddenly understood just why Dean sounded so worried. Not only had he seen Naomi, but he had lost Sam somehow too?

            “You let your brother go alone?” Henry demanded. He was starting to see red, though he knew he couldn’t hurt Dean right now. They needed him up and working.

            “He wouldn’t let me go, Henry!” Dean shouted. He was sounding desperate. “And the guy who took Sam said he would only take one of us. We should have guessed, I mean, it is downright suicide to work with Winchesters.”

            “Well, this guy isn’t dead yet. Calm down, Dean,” Henry said, hand massaging his forehead.

            “That’s the thing, Henry,” Dean took a ratcheted breath inwards, “he _is_ dead. I just found him.”

 

* * *

 

 

            Sam was stuck in purgatory. Henry was stuck in the damn bunker. Dean was just stuck. It had taken a few minutes just for Henry to calm him back down, which was an impressive feat considering just how much Henry himself had been freaking out about the whole thing. _That’s why you shouldn’t have let him go with you_ , he thought.

            “It isn’t your fault,” was what he said. _There is no way we are going to get him out_ , he thought. “You’ll find a way, you always do,” was what came out. The phone call had ended suddenly with a single word from Dean. A name.

            “Benny!” And then he hung up. Henry did his best not to crush the phone in his hand as the line went dead. He tried to call Dean back but a woman on a recording informed him that the line was busy. He called his other cell, and his _other,_ other cell, but Dean didn’t pick up either one. The process of the bunker’s destruction and then cleaning happened a second time. It wasn’t until the next day that Dean and Sam came back, Sam struggling through the door with Dean’s help. Henry waited until Sam was sitting down to reach forward, grab Dean’s shoulder to spin him around, and punch him, hard, across the jaw.

            “Ah, Henry, what the _hell?_ ” Dean asked, putting a hand up to his face. Henry was seething.

            “You didn’t. Fucking. _Call._ ” Henry spat. Sam’s eyes widened. He had never heard Henry swear quite like that before. “I have been here for almost a full day _waiting_ for you to get up off your ass and tell me you figured out how to save Sam. I thought you were both dead!” he moved forward like he was going to punch Dean again but Sam stood up and put a weak hand on him before he stumbled. The stumble took Henry a little out of his fury.

            “Sammy?” Dean asked, rushing to Sam’s side to hold him up. Sam tried to brush him off but just ended up stumbling again.

            “Sam, what’s wrong?” Henry asked. He stood in front of Sam, holding onto the boy’s chin so he could see into his hazel green eyes. He looked to the other brother when Sam failed to answer. “Dean?”

            “Second trial,” Dean said. “It hurt him worse than the first one did.” And with that, Sam finally passed out. Only Dean’s strong arms prevented him from crashing down to the floor. “Let me get him to a bed and we’ll talk. I swear.” He added when he saw Henry’s disbelieving face.

            It took Dean much less time to get Sam down the hall and into a bed than it had taken Henry, but he was still breathing hard by the time he was done.

            “Alright, sleep tight, sasquatch,” he said as he left the room and closed the door. He steeled himself up to go talk to Henry and almost bolted when he remembered his promise. He needed to talk to Henry. He needed to.

            Henry hadn’t moved from his spot by the table and his shoulders were still hitched up in fury. Dean could practically see the smoke billowing from his ears like in an old cartoon. He almost found it funny, if Henry’s face hadn’t been so damned terrifying.

            “Henry, I really am sorry,” Dean started.

            “Not good enough this time, Dean,” Henry said. He had his arms crossed and he stood tall, looking into Dean’s eyes without backing down. “You can’t keep doing this to me. I agree that I can’t leave this place yet. I understand that I am still healing, but you cannot keep me out of the loop.”

            “I know,” Dean said. And he really did. He could see now just how much it hurt Henry to worry. “Henry, I haven’t had any sort of, well, anyone worry about us in a long time. I’m not used to…” he trailed off.

            “People who care about you?” Henry asked. He was calmer now.

            “Well, yeah,” Dean said, looking down to the floor. Henry tried to bite back the question, but he couldn’t anymore.

            “And did Castiel care about you?” he asked. Dean’s head shot up, his eyes flecked with anger.

            “Don’t you dare talk about him,” he said, voice gruff. “Don’t you dare.” Henry saw that this conversation just wasn’t going to happen.

            “Fine, then tell me how you got Sam out,” Henry said. Dean shifted and shot Henry an annoyed glare.

            “I called a friend,” Dean said.

            “Yeah, thanks, that clears everything right up.” Henry rolled his eyes, “Is his name Benny?”

            “That’s the one,” Dean said, “I met him in, well, Purgatory. He’s a vampire. He helped me and—he helped me get out.” Henry’s eyebrows raised further and further at each part of the story.

            “You met a vampire in purgatory, who is now out of purgatory, who knows you well enough that you called him up and he helped you get Sam out?” Henry asked incredulously.

            “That’s pretty much it,” Dean said. “Only he didn’t come back with Sam like he did with me. He stayed behind in that lovely part of Satan’s ass-crack.”

            “So you are close enough to this vampire that he gave up his life here to save your brother? And I’m going to assume that Sam probably isn’t fond of him in the first place.” Dean’s silence was more than enough to validate both statements. “Dean,” he sighed, “I think you have always had people who cared about you. You just refuse to see it.” He walked away, not waiting to hear Dean’s answer.

 

* * *

 

 

            Henry was in the store rooms when he heard the loud sound of glass shattering down the hall. He shot up to action, grabbing a sword off of the wall nearby and making his way silently down the hall until he burst into the main rooms, ready to fight. Sam jumped back, shocked.

            “Whoa, Henry, what the fuck?” he asked. He didn’t sound good at all. Henry looked around and noted the broken beer bottle on the floor a few feet behind Sam.

            “I thought I heard… well, I heard that,” he finally said, pointing at the bottle with his sword, which now felt pretty stupid in his hands. He put the thing down on a side table, embarrassed.

            “Hey, Gramps here was totally going to take care of whatever monster had come in to kill you, Sammy,” Dean grinned and laughed. He took a deep sip from his own bottle.

            “Can we agree never to call me ‘Gramps’ again?” Henry asked, going into the other room for a broom and a rag to clean up the mess of beer.

            “Yeah, Dean, that is really weird,” Sam said, stumbling down to the table and sitting heavily in a chair. “After all, I’m fairly sure that we are both older than him.” Henry stopped in the middle of his sweeping. He hadn’t really thought about it, but now that he did, he was fairly certain Sam was right.

            “Oh, yeah,” Dean said, sounding like he had had the same mindset as Henry. “I know I am, but I didn’t even think about it. Wonder how many people have a grandfather who is younger than them?” Henry didn’t look at the boys. He just finished cleaning up the broken glass and returned a couple of minutes later to read a book. Sam had soup in front of him when he walked in and was arguing with Dean.

            “Dean, I’m fine! I need to be out, hunting,” Sam was shouting. He went to stand up and stumbled, almost falling over. Henry made a noise of frustration.

            “Yeah, that’s not going to happen,” Dean said. At least they agreed on that, Henry thought. Eventually Dean just grabbed Sam’s arm and ushered him down one of the hallways. “Come on, Henry.” He called over his shoulder. When all of them were together in the gun range, Dean picked up the handgun, examined it, and fired two shots directly into the paper form on the opposite end of the range. He handed the gun to Sam.

            “You hit that target, and we’ll talk about you getting back out there,” Dean said. Henry moved forward to say something but Dean put his hand up. He turned around to face Henry in a way that Sam couldn’t see and gave him a small smile. Henry closed his mouth and watched Sam. It was obvious why Dean had made this a requirement. He couldn’t even hold the gun up properly with one hand. He fired two shots and missed both times, by a large distance, hitting the wall instead.

            “Ok, this second trial hit you a lot harder than the first one did, Sam,” Dean said, taking the gun. “So just chill out and you can keep working on finding Kevin from here.” Sam straightened up and glared at Dean for a minute before walking away angrily.

            “Thank you, Dean,” Henry said.

            “Wasn’t for you, Henry, but sure,” Dean responded. Henry looked back at his eldest grandson and suddenly realized that even if Sam had made the shot, Dean wouldn’t have let him out. He had underestimated Dean again.

            “Hey, guys, I got a message from Charlie!” Sam yelled from the other room. Dean actually broke into a grin. He took off down the hallway, Henry close behind him.

            “What did she say?”

            “That’s she’s in the neighborhood, and she has a case for us,” Sam said, looking confused. Dean felt the same way.

            “How does she know she’s in the neighborhood?”

            “She tracked our location, but only within a few miles. She says we’re off radar.”

            “So we can make calls in here without being tracked?” Dean asked. He looked around the room fondly, “Man, I love this bunker.”

            “I’m sorry, but who is Charlie?” Henry asked, coming forward to remind the boys he was in the room.

            “Oh, Charlie’s the best,” Dean said, smiling more. He grabbed his coat off of a chair. “Come with us to meet her. She’s going to love you,” he added with a snort. Time-travelling Winchester in a secret underground bunker? Charlie was going to have a field day. “You’re coming too, Sammy,” Dean said. He gave Henry that look that didn’t leave much room for argument, but after the events in the shooting range, Henry thought he trusted Dean much more in keeping Sam out of danger.

            “Alright,” Henry said, picking up his own new, leather jacket. “Let’s go.”

 

* * *

 

 

           They were already down the road, Dean and Sam leaning against the car, Henry hanging back a bit, when Charlie’s yellow car pulled into view. She was smiling somewhat nervously as she got out with her bag and moved forward.

            “’Sup, bitches?” she said. The brothers smiled and Henry took that to mean that this was a fairly common way for Charlie to greet people. Sam and Dean each took a turn giving her a huge, warm hug, but Sam’s left him coughing slightly, forcing him to lean back against the Impala.

            “Whoa, Sam, are you ok?” Charlie asked, reaching for him.

            “Fine,” he answered, face plastered with a fake smile. She returned it uncertainly and suddenly realized there was another person by the car.

            “And who is this?” She asked brightly, shooting Henry a wide smile, then turning to look at Dean.

            “This is Henry,” Dean said, “Henry Winchester.” Charlie looked shocked, which was to be expected.

            “What, like a distant relative?” She asked, looking at him.

            “You could say that, I suppose,” Henry responded, smile playing at the corners of his lips.

            “Charlie, this is going to sound slightly nuts, but go with me here,” Dean said, sucking in a breath. “Henry is our grandpa.” He rolled the last word out with a strange lilt, like it wasn’t a normal word to say. It didn’t feel right on his tongue. Henry and Sam had been right, he was never calling Henry ‘Grandpa’, ‘Gramps’, or even ‘Grandpappy’ ever again.

            “Your grandpa?” Charlie asked, looking at Henry like he would let her in on the joke.

            “Yes,” Henry said, “I am from Normal, Illinois. 1958.” He pushed both of his hands into his pockets. He had never had this habit before, it had grown on him, or he had grown into it, since coming to 2013, but it just felt natural now. Especially when he was uncomfortable, which he was, with Charlie staring at him the way she was in disbelief.

            “No way!” She finally squealed. “You guys have a time-travelling grandpa? This is, like, a level of science-fiction I really didn’t think I would be able to live. Does this mean you guys got to have a ‘teach Henry about technology’ montage? Please tell me he gets all Captain America about cell phones and computers and stuff!” She was bubbling with excitement and Henry understood why Dean had laughed when he thought about how Charlie would react. It was actually pretty funny, even though he understood absolutely nothing that had come out of Charlie’s mouth just now.

            “Charlie,” Sam interrupted with a smile, “maybe back down just a bit. I think you’re scaring him.”

            “Oh!” She said, backing away and losing a bit of her smile. “Sorry, my bad. I just get really excited about time travel.” Henry smiled at her.

            “Not at all.”

            “Wait, so does this mean you can confirm what theory of time travel is true?” Charlie asked, facing Dean and Sam this time. “I mean, can we rule out _Back to the Future_ hand-disappearing since you two seem to be here? Or, wait, he could have had your dad and then left. Oh, or are we talking _Prisoner of Azkaban?_ A combination? Don’t tell me this is going to get as confusing as the time travel in _Lost_ did,” Charlie let out a breath. Somehow Henry didn’t think Charlie would mind if their situation was in fact as confusing as “ _Lost”,_ whatever that was. Dean chuckled.

            “This isn’t exactly our first round with time travel, Charlie,” Dean said. Henry was surprised, but Charlie looked less surprised than she really ought to.

            “Well, you’ll still have to tell me all about it so I have some really good arguments for my next time travel web debate,” Charlie said. Again, Henry understood about two words out of her mouth.

            “Will do. Now, Charlie,” Dean said, coming forward to put an arm around her shoulders. “Let us introduce you to the Men of Letters.”

 

* * *

 

 

            Charlie’s mouth had dropped open wider than Henry thought possible when she walked into the huge space that the three men called home. Dean showed it off like he had been the one to build the thing, but Henry enjoyed seeing the smile on his face. He wondered how the boys hadn’t mentioned Charlie before, considering how obviously close they were. He was confused by the T-shirt she was wearing, but he had been confused about many of Dean’s shirts initially as well. He thought that maybe Charlie was very similar to Dean, only she seemed much happier in general.

            “I can’t believe you guys have your own Batcave,” Charlie said when they were all sitting down at the table and she was still looking around, admiring.

            “Dean calls it that, too,” Henry noted. Charlie grinned at him and Dean in turn.

            “Oh, by the way,” Charlie said, looking at both of the boys, “there is this series of books I found by Carver Edlund? Did those… actually happen?” Henry looked to see that Sam and Dean were both scowling.

            “Books?” he asked.

            “Yeah, they’re called _Supernatural_ ,” Charlie said to him. “Thanks for saving the world, by the way. And sorry you have zero luck with the ladies,” she added with an apologetic glance at Sam.

            “We need to find every copy of those books and burn them,” Sam said, looking at Dean.

            “Well, they’re online now, so good luck with that,” Charlie said. But Dean picked up something else.

            “Did you say thanks for saving the world?” he asked, looking at Charlie intently.

            “Uh, yeah? The apocalypse? Thanks for stopping that.” This, Henry knew about. Sort of. He knew his grandsons had stopped the end of the world and was unbelievably proud, but did this mean that there were actual books he could read about the events?

            “I thought they only went to me going to hell,” Dean said, looking at Sam. Sam’s eyes widened.

            “He kept writing?”

            “YOU WENT TO HELL?” Henry demanded. Dean winced and looked at him.

            “Oh, yeah. We have sort of… both been.” Dean said. He looked severely uncomfortable with the path the conversation was taking.

            “So, Charlie,” Sam said, trying to redirect the conversation, “you said you had a case for us?”

 

* * *

 

 

            They were in the gun range for the second time that day. This time it was both Henry _and_ Sam who held back while Dean and Charlie stood by the concrete window.

            “Ok, now if you can hit that target, then—“ he was cut off by Charlie firing two precise shots into the head of the paper target at the end of the range. Henry’s eyes widened and Sam shifted in annoyance. Charlie handed the gun back to Dean with no small amount of pride. Dean sighed.

            “Alright, but if you are going to do a ride-along, it is time to lose the novelty T-shirts,” he said, shoving the gun into the back of his pants and leaving the room.

            “Does this mean we get to do a makeover montage?” Charlie asked, smiling her way past Henry and Sam as she followed Dean. Out in the hallway, Henry stopped her. He looked back and forth to make sure both Sam and Dean were out of earshot.

            “Those books you mentioned,” he began. Charlie’s eyebrow quirked up. “How do I find them?”


	3. Loving You With My Whole Heart

**Summary for the Chapter:**

> Henry gets his hands on the Supernatural books, bonds with Charlie, and Dean's angel finally makes an appearance. And yes, Dean, everyone knows he is YOUR angel.

**Notes for the Chapter:**

> I'm really excited to finally get to this chapter. I love writing Charlie, but I love Cas finally showing up. And making things go just a bit better than they did in the show, thank you very much. Enjoy!

            “Henry, what the _fuck_ were you thinking?” Dean yelled into the phone. Henry sighed, rubbing his pounding head.

            “He knocked me out, Dean,” he said. He wondered just how much sleep medication Sam had actually put in his tea, but based on his headache, it was a fair amount. “I couldn’t do anything, he put me to sleep.” He wasn’t even upset at Dean being as mad as he was. If he had been in Dean’s position, he would be ripping himself a new one right now. He heard Dean huff on the other line.

            “Fine. Not your fault.” Dean said.

            “Thank you.”

            “Yeah,” Henry heard the Impala in the background.

            “Is Charlie with you?” he asked, not hearing her voice. There was a pause.

            “Shit.” Dean said. “I left her with Sam. I was really upset, I didn’t even think about it.”

            “If she’s with Sam, she’s fine,” Henry said. He dug through the bathroom cupboard some more. “Hey, Dean, we aren’t out of Advil, are we?” He rummaged some more.

            “We ran out a couple of days ago. Why?” Dean asked. Henry heard the motor shut off.

            “The stuff Sam gave me to knock me out,” Henry said with difficulty. This headache was really bad. “It is creating a fairly painful headache. I don’t think I can actually stand up much longer.” Dean growled on the other end of the line.

            “I’m going to kill him,” he said. “Alright Henry, sit tight. I’m going to go get my bitch of a little brother and I’ll stop for some Advil on the way back, ok? Just go rest. We’ll be fine.”

            “OK, thank you, Dean,” Henry said. His head was hurting, but not enough to ignore how _nice_ Dean was being right now. Nice for Dean, anyway. And he never spoke to Henry this way. Maybe things were going to get better between them. He realized the line had gone dead after his ‘thank you’ and pulled the phone away from his ear just in time for a new strike of lightening to run its way through Henry’s brain. _Yes,_ he thought, _I think I’ll just rest for a while._

 

* * *

 

 

            Sam looked guilty, but not nearly guilty enough, when Henry saw him again. Dean and Charlie were both with him, Charlie looking uncomfortable, Dean just looking pissed as hell at Sam. Henry could sympathize. They were all sitting at the table researching when Henry walked in after his nap, looking ruffled. He hadn’t changed out of his button-down again.

            “Henry,” Sam started, but he was cut off.

            “Do that to me again, Sam Winchester, and you will find yourself missing an eyebrow the next day.” Henry responded sharply. Dean choked on the beer he was drinking, nearly spilling it down the front of his shirt and into his dad’s journal. Charlie hid her grin behind the little black rectangle she was holding. “Now what did you find out?”

 

* * *

 

            Henry didn’t really know how Sam had managed to talk everyone into letting him finish the hunt with them, but he was trying not to think about it. What if he was one of those pushover grandparents that did nothing but spoil their grandchildren? Whoa, that was a weird train of thought. Henry tried not to go there again. And he didn’t have to try very hard, because now he sat in front of a computer (which Charlie had shown him how to use while Sam and Dean were arguing about something) reading the history of his grandsons. The books were simple and easy to skim over quickly so he had already gotten through three of them. He was now just finding out why exactly Dean drove everywhere.

            He had never thought to wonder what either one of his grandsons might be afraid of. He knew they were terrified of losing each other, that much was obvious. He had also figured out that Dean probably feared losing Sam more than the other way around. Dean didn’t handle being left very well. A few nights ago Henry had found Dean on the couch, having fallen asleep in front of the TV he insisted they needed. Some medical show was playing and Henry found the button to turn it off. That’s when he heard Dean muttering.

            “Cas, Cas please,” his voice was broken. So completely broken it cut into Henry like a knife. He knew Dean masked his emotions, but he had never feared just how badly he had been really hurting. “Cas, we need you. _I_ need you.” Henry was entranced. He wanted to wake Dean up. After all, his body was shaking and tears were making tracks down his face, but he had the distinct feeling that Dean wouldn’t want anyone to have heard this. Any of it. Henry wasn’t sure he wanted to have heard it, either.

            “Cas, I love you, don’t do this,” Dean just kept talking. His voice was ragged and his breathing was shallow. “Hear me, hear me. This isn’t you. Be you. Please, be you again, Cas.” Henry couldn’t take anymore. He noted Dean’s phone on the table nearby and carefully walked over to make sure the volume was loud before heading into the other room and calling it. The sound of heavy guitars filled the other room of the bunker and Henry heard Dean wake with a start.

            “Henry,” Dean called, “you’re ass-dialing me, man.” His voice wasn’t as broken as before, but it wasn’t quite back to the teasing tone it held so often now.

            “I’m sorry,” Henry said, hitting the red button on his phone. “I didn’t mean to.”

            “That’s sort of the definition of ass-dialing,” Dean snarked.

            Henry had to let himself believe, after hearing Dean, that Sam had not lied about their relationship. Really, he had no reason to lie, Henry just never saw Dean as a person to be in love. He also wondered if anyone else really knew just how upset Dean was about Cas being gone. Dean never seemed to let anyone in. Anyone except Sam and Castiel, he supposed, and maybe Charlie.

 As he read further through the book, he made a mental note to ask Dean and Sam if they still used ‘christo’ when finding a demon. He thought it seemed like a useful idea.

 

* * *

 

 

            After the case, Charlie came over and stayed the night in the bunker. She could have had her own room, but she insisted on staying on the couch. She waited until Sam and Dean had both gone off to their own rooms before she invited Henry over to enjoy a beer with her on the couch. He brought the laptop he was using to read the supernatural books. He had gotten to John seeing boys at Missouri’s house and not saying anything to them and was starting to question just what his son had been like. The boys didn’t talk about him often, but it was usually positive. At least, the stuff from Dean was positive. And now, reading these books, Henry started to wonder if he deserved such praise.

            “Come over here, grandpa Winchester,” Charlie said, a teasing lilt to her voice. Henry found that he didn’t mind the nickname when she used it. It just seemed _right._ She handed him a beer as he sank down into the couch next to her.

            “Thank you,” he said, taking a sip.

            “So, I am just wondering,” she said, “how much these idiots have told you about themselves.” Henry laughed. Charlie really did know them well. She knew just how little he had been told about his own grandsons. He wondered if she had been waiting the entire duration of her visit to talk to him alone. He wouldn’t have been surprised.

            “Not much,” he admitted, taking another sip.

            “Sort of figured,” Charlie said, laughing. “The Winchesters are above and beyond the worst sharers that have ever been. No offense.” Funnily enough, Henry really hadn’t been offended. Charlie just had this tone that was so lighthearted that it was obvious she was only speaking her mind to be truthful, not hurtful. “How far are you through the books?”

            “John was with Missouri,” he said. He rolled the beer bottle around in his hands and started to pick at the label.

            “Ah,” she said. “That would explain why you are being more brood-y than usual.” Henry nodded.

            “It’s just that I blame myself. For the way he was to Dean and Sam.” Henry said. When he looked up at Charlie he found that she had already known that he felt this way.

            “It isn’t your fault,” she said, and Henry could tell by her frank voice that she meant it. “I mean, yeah, you left him, but the universe just doesn’t really play for Team Winchester.” Henry supposed he could see that. Charlie looked distinctly like some of her curiosity was about to overflow. Henry smiled at the look on her face.

            “You can ask whatever you want, you know,” he said.

            “What’s the deal with Dean and Cas?” she said, so quickly the words almost seemed to overlap. Henry blinked in surprise. He hadn’t expected her questions to relate to that at all.

            “The deal?” He asked. He thought he understood the question, but he didn’t want to be wrong.

            “The deal,” she said, then turned to face him more directly. “Like, ok, when Cas shows up in the books, Dean acts like he doesn’t like him at all, but pretty soon it is beyond obvious that they are madly in love and neither one of them ever does _anything_ about it. I tried to bring it up around Dean yesterday, but he sort of shut me down.” Through the whole explanation her arms had been gesturing wildly, trying to get her point across.

            “I wouldn’t bring Castiel up around Dean again,” Henry began. “He is very sensitive about that loss currently. As far as ‘the deal’ between them, while Dean has never told me himself, Sam informed me shortly after Castiel disappeared that they were, I suppose you would say, involved.” Charlie practically squealed. Only a pillow across her face stopped her from shouting loudly enough to wake the brothers up.

            “I _knew_ it!” She whisper-yelled and Henry was again surprised by her reaction. She was so enthusiastic about so many things, and Henry found he really enjoyed it. “I knew they were in love! When did it happen?”

            “Apparently in the year Dean and Castiel spent in purgatory,” he said. Based on Charlie’s face, Dean had informed her of his trip.

            “I can’t believe he didn’t tell me!” She threw her arms up into the air and fell back against the couch. “I’m going to kill him.”

            “Charlie,” Henry said, sitting up urgently. “You can’t tell him I told you. I don’t even think he knows that I know. I can’t break his trust now, when he is just starting to let me in.” Charlie laughed and tossed an arm out towards him.

            “Oh, relax Gramps, I’m not going to tell him it was you,” she said, “I have my own ways of making him talk.” Henry decided he really didn’t want to know what those methods were.

            The two stayed up talking for most of the night, jumping from topic to topic quickly. Charlie confused him sometimes, referencing things he’d never heard of, but he enjoyed the conversation. It was the first time he had laughed since he had gotten to 2013 and he found himself with a stomach ache at one point he was laughing so hard. Charlie asked him about his life in Normal, and he asked her about her ‘computer things’, though he didn’t follow a single word she said. It was companionable and easy, so Henry found that neither of them minded when they fell asleep on the couch, Charlie leaning on his shoulder.

 

* * *

 

 

            “So you think you actually found Metatron?” Henry asked. He was reading the same book Sam had found the Native American symbol in earlier, but there wasn’t much additional information inside. Now Dean was talking quickly on the phone, thoroughly worried about his younger brother.

            “Well, the whole place seems off,” Dean said. “I’m heading back to the room now and—oh my God, Sammy!” There was the sound of pounding feet and Dean yelling.

            “Dean, what is it?” Henry shouted to get his attention, “Talk to me. What’s wrong with Sam? Breathe, Dean.” Henry heard Dean breathe inwards deeply.

            “He is… just lying on the floor in the hallway. I don’t know. He is so hot, Henry. He’s burning up.” Dean grunted loudly. “Henry, I have to hang up on you for two minutes. Just two. I have to get him into our room and I need both hands.”

            “Call me back when you get there or I will kill you myself,” Henry said and he was the one who hung up.

 

* * *

 

 

            Dean had called back, only for a minute, to tell him that Sam was ok, they were both fine, but Sam was still a little delirious. He promised they would be back soon and Henry thanked him for calling. The fact that Dean was willingly calling him and even calling him _back_ as promised was such a far cry from where they used to be that Henry could hardly believe it. Henry spent the rest of the night worried, as he always was when the boys were gone, but he was not overly worried. He felt confident now that Dean would call, which is why he was surprised when he heard the sound of the Impala pulling up outside. He figured Dean and Sam would be longer. The engine cut off and Henry walked towards the stairs to meet the boys as they came in.

            “Sam, you aren’t helping,” Dean grunted. He sounded tired.

            “Sorry!” Sam stumbled in backwards, arms out like he was ready to catch something. Dean came into view shortly afterwards, carrying a figure in a trench coat who wasn’t moving. Dean was struggling under the weight of the man, but he refused to let Sam put a hand on him. Henry adjusted his stance from welcoming to worried, trying to understand what had happened since his last phone call with Dean.

            “Move,” Dean growled, and Henry couldn’t tell if it was directed at him or Sam, as both of them were now standing side by side, blocking Dean’s way as he dragged the unconscious man, who also appeared to be covered in blood, down the hallway and into a guestroom next door to Dean’s that had been made up since Henry had arrived. Henry followed after tentatively, but Sam hung back. He got to the door just in time to hear Dean mutter, “Come on, Cas, wake up.”

            Henry wasn’t surprised. He had his suspicions that this was Cas since he had seen the trench coat. He was already far past _Lazurus Rising_ in his quest to read the Supernatural books, and it turned out Carver Edlund’s description was far from inaccurate. The angel looked exactly as Henry had imagined him. Dean seemed to not notice Henry’s presence. He ran a hand through Castiel’s hair delicately, rubbing a thumb across a spot of dirt on the angel’s forehead as he went. The gesture was intimate, as though done many times. Henry felt like he was looking through a window shouldn’t have been. He retreated without saying another word.

            In the other room he found Sam was not doing well, which was to be expected based on Dean’s earlier phone conversation. He was sitting down and looking extremely haggard, the rings under his eyes even more prominent than they had been the day before.

            “Where did you find him?” Henry asked. He could only assume it had been the brothers who had happened upon Castiel, as the angel seemed currently incapable of being conscious, let alone trying to locate two humans out of billions.

            “He appeared in front of our car,” Sam said. He sounded shaken. “Dean almost hit him. He never would have forgiven himself.” Sam shook his head, letting his long hair whip softly around his shoulders. Whatever he had woken up expecting today to be like, he had been very, very wrong.

            “Will Dean be ok?” That was really the only thing on Henry’s mind at that point. Dean had been so broken up after losing Castiel, and now suddenly getting him back? Henry knew from experience that Dean was slow to give his trust to people. Then again, it probably worked differently if you were Cas. He just got that feeling.

            “He always comes back,” Sam said matter-of-factly. And really, he didn’t even have to think about it. Cas always came back, which was something Dean tended to forget with all those abandonment issues. No matter how many times his angel left, he always came back.

            “That isn’t what I asked,” Henry said, trying to get Sam’s focus, “Will _Dean_ be ok?”

            “Oh, Dean,” Sam’s eyes looked a bit less clouded over for a second while he thought about it. “Dean is always ok.” Henry knew from experience and also from his reading that this was not even remotely the case, but he let it drop. Sam looked utterly exhausted and Henry really didn’t know how he managed to keep the conversation as on topic as it was.

            “Let’s get you to bed, Sam,” Henry said, coming forward and holding out his hand to support Sam while he stood up. Getting the giant Winchester into bed wasn’t as hard as it had been the first time he did it, as Sam was really still fully conscious, just not responding to conversation well. Henry really did enjoy leading his gargantuan grandson to bed. It made him feel sort of like a father again. Well, a grandfather in this case, but the emotion was mostly the same.

            When he emerged from the room he found Dean on the couch gulping down a beer. Henry hovered around the edge of the room, trying to get a read on how Dean was feeling just then. He really had no idea what to expect after the strange reunion, so he opted for avoiding the subject, just for the time being.

            “What happened at the hotel?” he asked, not making any moves forward into the space.

            “We found Metatron,” Dean said. He sounded bitter.

            “Isn’t that good news? You found what you were looking for,” Henry said. Now he took a small step inside the room. Baby steps, approaching Dean like a wounded animal.

            “He isn’t exactly what you would call heavenly,” Dean said.

            “From what I’ve heard, isn’t that a good thing?”

            “Sure, unless you need some angel help and the angel in question is a damn agoraphobe who hasn’t left his fucking motel room in 2,000 years.” Dean sucked down half of the remaining beer in his bottle. “On the other hand, he brought Kevin back. And we know the third trial.” Henry was shocked. He hadn’t expected this much to have happened with the way Dean was acting.

            “You know the third trial, you have your prophet back, and you have your angel back and you are still moping around like some kid stole your candy?” Henry asked. He walked a few more steps into the room until he could look at Dean directly. He looked tired.

            “s’not my angel,” he muttered, not meeting Henry’s eyes.

            “Yes he is, and everyone knows it so you can stop trying that one,” Henry said, rolling his eyes. Dean looked surprised.

            “And you’re cool with that?” Dean asked, looking up at Henry.

            “Of course,” Henry answered coolly. He didn’t mention how long it had _taken_ him to be cool with that, but that part of the sentiment didn’t matter.

            “It’s just, the last time I saw him,” Dean breathed in raggedly, “he wasn’t really… _Cas._ And then he left. Again.”

            “But he came back,” Henry reminded him. Dean shrugged.

            “He does that.” Before Henry could say anything else, Dean was up out of his seat, “Goodnight, Henry,” and then he was gone.

            “Goodnight, Dean,” Henry whispered into the empty air.

 

* * *

 

 

            The next day, Henry made sure he was the only one hanging around Castiel’s room. Both of the brothers were in the main area doing more research on the latest trial that Metatron and Kevin had given them, but Henry wanted to talk to the angel. He sat in his room across the hall and waited to hear the tell-tale sound of the heavy door opening. It was fairly late into the morning when he finally did. Henry jumped up off of his bed and ran out his already open door, almost running into Castiel.

            The angel stiffened sharply at the man he didn’t recognize and his angel sword fell down into his palm naturally. Henry noticed and fell a few steps backwards.

            “No, it’s ok,” he said, holding his hands up in surrender, “I’m a friend. I’m Henry Winchester, Sam and Dean’s grandfather,” he noticed the way Castiel’s eye twitched at Dean’s name. He also noticed the angel unstiffening his posture slightly, moving out of a battle-ready stance. He was still wary, obviously, but Henry wasn’t worried he would kill him on the spot anymore. He probably should have figured that pouncing on an injured angel who had no idea who you were was a terrible plan, but no going back now.

            “How are you here?” Castiel asked and wow, Henry was not prepared for that voice. Sure, the books described it as gravely and deep, but it also rang with so much contained power. He could feel the thrum of it in his bones.

            “I got here a while ago,” Henry said. He lowered his hands experimentally and when Castiel didn’t attack him on the spot, he let them fall completely. “I jumped forward in time to stop a Knight of Hell and I was led to Sam and Dean. I was injured in a fight. They took me in.”

            “How did you manage to time travel?” Castiel asked. He looked Henry up and down, “you are only human.”

            “I drew on my soul,” Henry answered. Castiel seemed to accept this much more readily than Sam and Dean had. Although, that wasn’t completely shocking considering how old Castiel was and how much he had seen in his lifetime. Henry had underestimated just how strange it would be to have this conversation. Castiel made a move to go past him.

            “Now wait just a second,” Henry said. He didn’t put a hand on the angel to stop him, deciding that was probably not the best plan, but his voice alone seemed to stop Castiel. “Look, I don’t care where you have been, or what you have been doing, but I do care about Dean. You hurt him. And I don’t take well to people hurting my grandsons. If you ever hurt him that way again, angel, I will find a way to hurt you myself.” Henry was annoyed to see the look of amusement on Castiel’s face. He knew he was no real threat to the angel, but amusement was just rude.

            “It is obvious you are related to them,” Castiel said, not smiling, but Henry could almost hear it on the cold voice. “Your loyalties to family and your tendency to threaten are the same as Sam and Dean.” Ah, so that was what the amusement was for. Henry thought back to his threat and started laughing.

            “I don’t know when I became so much more like them,” he said, looking down. Castiel tilted his head at Henry.

            “You have always been like them. You are a Winchester.” And with that, he did get past Henry and into the main room where Sam and Dean were.

 

* * *

 

 

            “My wound isn’t healing as quickly as I’d hoped,” Henry heard as he entered the room. He had taken a couple of minutes calm himself down and get ready to be in the same room as what was bound to be an unnatural amount of tension. He walked in to Castiel was sitting down near Sam, holding his stomach. He looked uncomfortable. “But I am getting better. And you’re getting worse.” Henry knew it was the case, but to hear Castiel say it made the whole thing seem more real.  Sam was not improving at all. Giving him time wasn’t enough to help.

            “Well, two trials down, one to go.”

            “And the third trial, you know what it is?”

            “Yeah, I, uh, have to cure a demon,” Sam sounded about as confident in being able to do that as Henry had when he had first heard the third trial.

            “Of what?” Castiel asked.

            “That’s what we’re trying to figure out,” Sam said. Henry noticed the helpless gesture at the books spread all across the table.

            “Where is Dean?” Henry asked, coming forward to join the conversation. He had been sure that both his grandsons were in the room but now it looked like only Sam had been there. Castiel looked down.

            “Soup’s on!” Came Dean’s voice. He was holding a tray in his hands which he put down in front of Sam. He picked up the bottle of beer on the tray, “I think that’s, yup, still good.” Sam looked down at the tray and Henry rolled his eyes in Dean’s direction.

            “A half-drunk beer, jerky, and three peanut butter cups?” Dean shifted.

            “We’re a little low on supplies,” the older Winchester admitted. _No shit,_ Henry thought. “I’ll do a run.”

            “I’ll come with you,” Castiel said, standing up. Henry noticed that in the whole time Dean had been in the room he had not once acknowledged Castiel, a big jump from the way he had been the night before. “Dean, I’m sorry.” Henry noted the begging look Castiel’s eyes had now. It was so strange to see the change. When he had been talking to the angel, his blue eyes had been hard and almost alien, not the open, broken things they were now, displaying so much emotion. So much need for Dean to just look at him.

            Dean rolled his shoulders and looked up, finally meeting Castiel’s eyes. “For what?” _Oh, here we go,_ Henry thought. He could already tell this conversation wasn’t going to go well. He looked to Sam for cues on how he should react in this situation, considering he had never seen the two interact before. He was oddly uncomfortable just standing there in the silence. It seemed that now Dean had decided to look at the angel, he wasn’t going to stop. They just stared at each other silently. Sam was looking hard at the table.

            “For everything,” Castiel said, still looking at Dean. Still pleading with those eyes. Henry didn’t know how Sam could take it.

            “For everything?” Dean said, “Like ignoring us?”

            “Yes,” Castiel said. He sounded ragged, like he knew this conversation wasn’t going to go well either, which didn’t surprise Henry. Considering how close Dean and the angel were, Henry was sure Castiel knew Dean even better than he did.

            “Or bolting with the angel tablet and losing it because you didn’t trust me?” Dean sounded disappointed but he still wouldn’t look away, “You didn’t trust _me_.” Castiel looked down and Henry looked to see that Sam was still sitting firmly. What was wrong with him? This was obviously an intimate moment. He and Henry shouldn’t be here. Henry cleared his voice and received looked from two pairs of similar eyes.

            “Sam, would you come take a look at my computer?” he asked, trying to think of pretty much any excuse to clue Sam in, “I just can’t figure out how to find that web-thing you were talking about.” Henry was annoyed at having lie. He had actually gotten quite good at using the computer, especially after Charlie’s tutorials. Now he had to play the ‘from a different century’ card and it was driving him crazy.

            “Uh, yeah, sure,” Sam said, standing up carefully and following Henry out around the corner. They stopped just outside the door. “What’s the deal, Henry?” Sam asked, keeping his voice at a whisper. Henry shushed him.

            “I just don’t understand, Cas,” Dean was speaking more quietly, more tenderly now. Henry assumed he had let his shoulders fall out of their defensive positions a bit. “How could you not trust me?”

            “Dean, I am so sorry,” Castiel also sounded more open with the conversation just between the two of them now. “I don’t know how to tell you how sorry. I was so afraid. My mind hasn’t been my own in months. I didn’t know what to do.” Henry heard the sound of footsteps and he wondered which person had stepped closer.

            “Henry, we shouldn’t be eavesdropping!” Sam hissed. Henry waived him off. He had never had a chance to be exposed to this relationship before, and he felt such a thrumming need to know this part of Dean’s life. He still felt so protective, and Dean had been so hurt before. He just needed to know Dean would be alright.

            “Cas, I’ll forgive you. You are forgiven if you just tell me what happened,” Henry heard a sniff and suspected it was Castiel’s, though he had a hard time picturing the angel crying.

            “Naomi, she” Castiel sucked a rough breath in, “she tortured me. She made me forget when I met her. I didn’t know what was happening.” He sounded like he was on the edge of losing it.

            “Tell me, please,” Dean whispered so quickly Henry almost didn’t catch it.

            “She made me practice ki-killing you. A thousand times. Dean, I killed you so many times.” Henry heard what sounded like Castiel falling heavily into a chair, so fast and hard he wouldn’t have been shocked if Castiel’s knees had given out while he was standing. Hell, it hadn’t even happened to Henry and his knees still felt weak. Sam looked like he had been hit across the fact with a baseball bat.

            “Cas, you didn’t kill me,” Dean said, his voice completely different than it had been at the beginning of the conversation. Now he sounded like he was begging Castiel. “Not when it mattered. You didn’t kill me, I’m right here.” Henry took a breath and risked a look around the corner. Castiel was sitting heavily in a chair, tears running down his cheeks, and Dean was in front of him on his knees, carefully stroking the angel’s face, sort of like he had been the night before.

            “But Dean, I hit you. I just kept hitting you. What if I hadn’t stopped? I could have killed you!” Castiel looked down at his hands in disgust. He was breathing hard again. Dean put his hands on either side of the angel’s face and forced their eyes to meet.

            “You stopped.” He said, with an air of finality. “You stopped when it mattered, and now you are back here with me. And that bitch Naomi has one hell of an enemy.” Castiel still looked miserable when Dean did something Henry wasn’t completely expecting. He leaned forward and kissed Castiel. For a moment, the angel didn’t respond. He just sat there rigidly while Dean reached behind him and ran a hand down the ridges of his back. Finally, he reacted.

            The angel’s hands went up and around Dean’s form, hugging him more closely. He kissed desperately, like he had been underwater and Dean was his burst of air. One hand grabbed tight to the back of Dean’s neck and then moved up into his hair and Dean groaned. At this point, Henry agreed with Sam. He turned around and grabbed the tall Winchester’s arm and moved them to another room, more than eager to let the couple be alone for as long as they needed. 

**Notes for the Chapter:**

> Chapter title from White Blank Page by Mumford & Sons


	4. I See Trouble On the Way

**Summary for the Chapter:**

> Castiel finds out about Henry's reading material, but hey, he wasn't going to be able to hide it forever. Plus, something about the world's most disgusting jigsaw puzzle?

**Notes for the Chapter:**

> One more chapter for this part of the Henry verse and we will have reached the end of season 8, and the end of part 1! I have more than half of part 2 written, so don't fear. Please comment and subscribe so I know I am posting for a reason. Thanks for reading!

            Eventually, Castiel did leave after all to get supplies and Dean wandered into the living room where Henry had his computer open and Sam was reading a record belonging to the Men of Letters. Both of them were silent until Dean cleared his throat.

            “Cas, uh, left to get some supplies,” he said. His voice sounded raw and his lips were red and swollen. Both his hands were in his pockets and he was looking down.

            “He’ll be fine, Dean,” Sam said, not looking up. He could hear on Dean’s voice just how much he probably hadn’t wanted Cas to leave in the first place.

            “’Course he will,” Dean said, sniffing like he was personally offended, “he’s tough for a nerdy dude with wings.” Sam rolled his eyes at the familiar nick-name. Henry stayed quiet, flipping through some more information on the computer.

            “Do we have a room 7B?” Sam asked, looking up from the records he was reading. Dean pulled a face like he was thinking.

            “Yeah, why?”

            “I think we need to check it out,” Sam said. He stood and made his way down the hall. Henry stood to follow him but Dean stopped him just before he left the room.

            “Thank you,” he said, not meeting Henry’s eyes, “for, uh, getting Gigantor out of the room. He doesn’t, um, tend to pick up on hints.”

            “Of course, Dean,” Henry said, “you needed space. I gave it to you.” He started to walk out past Dean again before he stopped himself. “And I’m glad that you made up. He seems special to you. You should hold on to what’s special.”

 

* * *

 

 

            The dungeon had been an interesting find. Not what any of them were expecting, really. The chains were very strange and Henry had no doubt they were for a specific, demonic use. Finding the tapes was more helpful. They got back to the main room just in time for Castiel to come back with supplies. He was quiet, but not bashful. He just didn’t seem like the type to talk constantly.

            “Can I help you with those?” Henry asked, pointing at the bags in Castiel’s hands. He relinquished one to Henry willingly and with a nod of thanks. Dean followed them both into the kitchen without a word. Castiel and Dean walked side by side and when Henry glanced back he noticed their fingers lightly intertwining. Not hand holding, per say, just a need to be touching. Henry found himself watching the two of them as they put away supplies. They moved together like there was some sort of magnetic pull that kept them connected at all times. They constantly looked like they were about to crash into each other but one of them or both would gracefully move before any kind of collision could happen.

            Not that they never touched. Henry had never seen Dean be so physical with a person, perhaps besides Sam, but this was a very different kind of physical. And he got the feeling Dean was trying not to be obvious, like he would touch Castiel more, if he could. Little things constantly happened, Dean touching Castiel’s shoulder lightly as he moved around him, a tap on the elbow, even moving Castiel by his hips when he needed to get to a cupboard. To Henry it just looked like a need to establish that Castiel was really there, that he hadn’t been imagined. Once, when they both thought that Henry probably wasn’t looking, he saw them kiss quickly as Dean crossed in front of Castiel to get to the fridge. It was a quick peck, familiar and light, but both of them smiled as they pulled away.

            “Alright, we’d better watch that movie,” Dean said, sounding somewhat reluctant. All of the groceries were put away so there was no more need of the familiar dance the two had been doing.

            “There’s a movie?” Castiel asked. Henry was surprised, but he had forgotten Castiel hadn’t been there for that part. It was so strange, but even after catching looks of the two for the past 15 minutes, he couldn’t remember Castiel ever not being with them. Dean just seemed so much more alive and focused with him there.

            “Oh, yeah, found it while you were gone,” Dean said. “You know what we should do?” Dean smiled and started going for one of the cupboards.

            “What?”

            “What?” Henry and Castiel asked simultaneously. Castiel turned and smiled slightly at him, shyly.

            “Let’s make this a real movie, since it is probably your first, Cas,” his hand came out of the cupboard with a foil container labeled popcorn.

            “I’ve watched television before, Dean,” Cas said, but he was smiling still.

            “Sure, but you’ve never watched it right!” Dean went to work on getting the popcorn popping. The little foil container soon started filling up, expanding at each loud popping noise as the kernels heated. Other than the sound of the popping corn, the kitchen was silent. Castiel and Dean seemed more than content to live in the silence, but it was feeling heavy on Henry.

            “So, Castiel,” he started. The angel tore his eyes away from Dean almost like it actually hurt, “do you even eat human food?” As far as he had read in the Supernatural books (which he was still keeping secret from the boys) Castiel did not indulge in almost any human activities, and Henry had yet to read about him eating.

            “Dean enjoys showing me what he calls ‘perks’ of being human,” Castiel said. “I enjoy coffee and burgers, and I readily appreciate any variety of pie.” Dean grinned behind him.

            “That’s right,” Dean said, “we’ll have to get some pie.”

            “I tried to get you some down at the store when I got the rest of our things,” Castiel said, a hard edge coming across on his voice, “but the boy there said they had none.” Henry laughed at the frustrated look on Castiel’s face and Dean readily joined in.

            “I have never seen you look so upset over something like pie,” Dean said between laughs.

            “I wanted to be able to bring you pie,” Castiel responded like it entirely explained his very emotional reaction.  
            “That’s fine, Cas, you can get some next time,” Dean smiled and ran his finger along Castiel’s arm quickly before turning to take the finished popcorn off of the stove. “For now, I have a new treat to introduce you to.”

 

* * *

 

 

            The movie was something Henry was much more used to, which made sense, he supposed. The thing was made in his time. It was so much simpler than movies now. Sam had made Henry watch a movie called _Avatar_ just a few weeks earlier. It had been astounding to see how far things had evolved in terms of movie making, but it was just too much for Henry to take in at once. It all looked so real! But this, this movie was much more manageable.

            The priest, Simon, was obviously distressed about what was about to happen. He shifted and looked uncomfortable, especially when asked directly about the exorcism. Henry jumped when he saw the camera person’s reflection.

            “Wait, is that Abaddon?” Sam asked, leaning forward.

            “Nah, not killy enough,” Dean said. Henry felt his heart drop a bit at the sight of his friend.

            “It’s got to be the chick she possessed,” Sam said.

            “Josie,” Henry said quietly. “Her name was Josie.” No one responded after that but he noticed Castiel turn to look at him, sympathy apparent. The movie continued, full of screaming. Finally the room opened up and Henry noticed something even as Sam put the thought into words.

            “Hey, those look just like the chains in our dungeon!”

            “In your _what?”_ Castiel’s eyes opened more as he turned to look at the brothers with obvious confusion. He went equally ignored, as Henry had.

            “Demon on a leash – cool.” Castiel turned to look at Henry, who was busy hiding a smile at the comical expression on the angel’s face. The man shrugged and Castiel finally turned back around to the screen, which was producing noises that quickly wiped the smile off of Henry’s face.

            “Well, that was weird,” Dean said, “with three exclamation points.” Henry had to agree. He had studied traditional exorcisms and that was certainly not one.

            “That wasn’t a normal exorcism. They changed the words.” Sam said.

            “I believe ‘lustra’ is Latin for ‘wash’ or cleanse’” Castiel added.

            “Oh, yeah,” Dean scoffed, “’cause the most freaky thing was the vocabulary. What about the bloody high five or the chest burster? Anything else on the film, like director’s commentary, sequel maybe?”

            “Yeah, listen to this,” Sam picked up a file, “the older priest, Max Thompson, bit the dust in ’58, but the younger one is still alive and still in St. Louis.”

“You think this kind of weird is worth the drive?”    

“Dean, everything in these folders – the deals, the possessions, all of it – we’ve seen that before. But that – that was all new. Yeah, it’s worth the drive.” Henry was starting to feel like they were forgetting he or Castiel was even in the room as they started to leave. Castiel didn’t seem to be as bothered by it, though, and he simply stood up to join them.

            “No, you’re staying here,” Dean said, pointing at the angel.

            “Sam is more damaged than I am, Dean,” Cas was getting that lost look in his eyes that Henry had seen earlier when he was begging for Dean’s forgiveness.

            “Sam is the one doing the trials, I need him there,” Dean said.

            “And you don’t need me?” The words were quiet, unsure. Henry looked down, once again uncomfortable to be in the same room with the two, who were having some sort of staring contest across the table.

            “I need you… to stay and get better,” Dean finally said. His whole stance changed with the last part of the sentence. He shoulders lowered, his eyes opened up. Now Dean was back to begging Castiel. He was worried. Why did it seem like they were always begging each other to just be safe?

            “And what about me?” Henry asked. He stood up and looked at Sam and Dean in turn.

            “What about you?” Dean asked.

            “Am I staying here, yet again, to get better?” Henry asked. He had previously been feeling somewhat confined, but now he felt absolutely trapped in the bunker. “It has been months, I am better. I can leave. And this is connected to my past.” Dean and Sam shared a look. Henry may have only known his grandsons for a few months, but he knew that look. So much for getting out.

            “Henry, I just think that-“

            “Fine.” Henry cut Sam off before he could finish his stumbling sentence. “I’ll stay here. Wait for your call. Like a good little research boy.” He crossed his arms and refused to drop his glare. Dean shifted uncomfortably.

            “Let’s roll,” he finally said, grabbing his jacket off of the chair behind him. Castiel went around the table to meet him.     

            “If you will not allow me to go, you will promise me that you will stay safe,” the angel said, moving directly into Dean’s personal space. _Seriously,_ Henry wondered, _how could Sam stand to be in the same room as them all the time?_

            “I promise, Cas,” Dean rolled his eyes before noting the worry he read in Castiel’s expression. He looked at Henry, who was still watching the two of them, before he seemed to decide it didn’t really matter, and then he moved forward and kissed Cas. It was a relatively quick one, sweet and soft. Dean moved his hand behind Castiel’s head and held it steady when he broke away and said with much more emotion, “I promise.” Cas nodded and moved away from the hunter. Within minutes, the boys were gone and only the barest hint of the sound of crunching gravel could be heard as the Impala drove away.

 

* * *

 

 

            Cas and Henry were silent for a while after the boys left. Henry looked at Castiel; Castiel stared at the door Dean had just walked out of. There was a distinct heir of _longing_ dripping off the angel and Henry wondered if Castiel had been like this the whole time he was away from Dean. He also wondered if the two idiots knew just how suited for each other they were; he wanted to find a video of the way Dean had been pining after Castiel so he could compare just how similar their stance was when they longed to be near one another.

            Finally, Henry couldn’t handle the silent staring anymore. Even with no one in the room for Cas to stare at, it felt odd. “Well, I’m going to go do some reading,” Henry turned back to the table and grabbed his laptop before going to the living room and settling into a chair.

            “What are you reading?” Castiel’s voice surprised him, almost causing the open computer to fall to the floor.

            “Jesus, don’t sneak up on me like that!” Henry scolded. Castiel was standing in the doorway looking lost and out of place. “Don’t just stand there, come and sit down. And sorry. About the swearing. Should I not swear?” Castiel shifted back and forth again before heading into the room and sitting carefully on a chair across from Henry.

            “Dean and Sam certainly don’t alter their language for me,” Castiel said. “So don’t worry about it. And thank you. For offering the chair.”

            “Don’t thank me,” Henry waved his hand. “As far as I can tell, this is just as much your home as it is mine. You should feel comfortable.” He noticed Castiel’s small smile. He couldn’t believe how different the angel was when he was away from Dean. He was so much less comfortable, much less willing to express emotion, much less… human. He got the feeling Dean had even influenced this already inhuman way of interacting, and that Castiel had probably been even more robotic before.

            Who was he kidding? Of _course_ he had been less human. Henry had read those books. He was still trying to work out how the angel had gone from the stiff soldier of the books that Dean only sort of tolerated to… Cas.

            Henry was about to ask Castiel as much but the angel spoke first. “If you don’t mind me asking,” Castiel said, settling into the chair a bit more, “why have you not tried to go back to your own time?” Henry readied himself to be indignant but when he looked up, all he saw in Castiel’s blue eyes was curiosity. He wasn’t trying to be cruel, he wasn’t attacking Henry, he just wanted to understand.

            “I think it was Dean who convinced me,” Henry said, somewhat reluctant. Neither of his grandsons had asked yet but Henry had been waiting to deal with this conversation. He had not imagined he would have it with an angel who was sleeping with his eldest grandson, but that just seemed like the way his life was going these days. “When we were trying to save Sam, back after I first got here, he told me that if I went back I could change their whole lives. They might even cease to exist. And after knowing them… I could never risk that.”

            “You are wrong,” Castiel said after a few moments of silence. Henry’s eyes shot up.

            “Excuse me?”

            “You would not change their lives; they would not cease to exist, because their path in history can’t be changed. It is set. No matter what you did, you would not get back to John.” Henry swallowed thickly. The angel had hit the nail on the head when it came to what Henry was thinking about. Always John. He just wanted to know his son and he had missed it. Although, after reading the books about John that he had, Henry wasn’t sure he would have wanted to meet him all grown up. He seemed less and less like the kind of man Henry had wanted to raise. His eyes fell back to the computer screen, but they were glazed over. He couldn’t read. He could never go back home. At least it had been confirmed. “I’m sorry, have I upset you?” Castiel looked worried and he leaned forward.

            “No, you just… just confirmed something for me,” Henry sighed. “Thank you, Castiel, for telling me.” Cas nodded softly and leaned back into his chair again.

            “So what are you reading?” Castiel asked again. Henry thought it might just be that Castiel was trying to keep up a normal conversation, but he had the sense that the angel was also desperate to have Henry’s approval. Unfortunately, Henry wasn’t entirely proud of his particular reading material.

            “Look, the boys don’t know,” he began slowly, “but I’m reading their books. The _Supernatural_ books.”

            “You mean the Winchester gospels?” Castiel asked. Henry barked out a quick laugh.

            “Is that really what they’re called?” The name just seemed so absurd. To have his name in front of the word ‘gospels’ felt all kinds of wrong. “They just don’t tell me anything, and I wanted to know. About them. Their lives.”

            “I could tell you some also, if you wish,” Castiel said.

            “Really?” Henry was more interested now. He really had wanted to know about some of the things he had read from a person who was actually there. He had, again, hoped that it would be a conversation with one or both of his grandsons, but he was more than happy to let Castiel fill in some blanks.

            “Yes, I will,” Castiel said. He suddenly cocked his head. “But I’m afraid it can’t be right now. I need to meet someone.” He stood up to leave, his trench coat falling into place behind his knees.

            “Wait, Dean said you were supposed to stay here,” Henry said, standing also. “Who are you meeting?”

            “Metatron,” Castiel said. “We have things to discuss. I will explain to Dean when I get back. I enjoyed talking to you, Henry.” The angel ducked his head in an awkward sort of almost bow and then he was gone.

            “I can see how that is really annoying,” Henry grumbled. He walked back to the couch sullenly and opened up his computer, ready to start a new book in the Winchester Gospels: _The End._

 

* * *

 

 

            Henry was still busy reading when the boys got back. He had almost finished his least favorite book this far. He was not a fan of this broken future Dean had been sent to. He hated reading about how harsh Dean had become. He was so dark, so unyielding. Castiel was almost as bad. Henry thought reading about the drugged-up fallen angel would probably be much worse if he knew Castiel better, but even knowing him the little bit he did, reading about him so broken was hard. Henry couldn’t imagine how it had been for Dean to have seen it.

            “Cas? Henry?” Dean called into the bunker as soon as he opened the door. Henry shifted uncomfortably. So Castiel _hadn’t_ called Dean to let him know where he was. This wasn’t going to be a particularly fun conversation.

            “Just me,” Henry called, swallowing. Dean walked into the room. He was still in his suit. His eyes were wide open and verging on some sort of unpleasant emotion.

            “Where’s Cas?” Henry sighed and closed his laptop.

            “He said he had to meet someone,” Henry said. Dean bristled.

            “He just left?”

            “He said he would be back,” Henry tried to add, but who was he kidding? Dean wasn’t going to be calm about this.

            “And you just –“

            “Before you get your ass any more scrunched up,” Henry cut in, “how about you call him?” Dean shut his mouth with a snap.

            “Fine,” he left the room, pulling a phone out of his pocket. Henry let out a breath. _Well, that went slightly better than expected._

            “So, what did you find out?” Henry asked Sam as he entered the room. Henry noted that he looked distinctly worse than when he left. Instead of answering, Sam held up a small tape.         

            “…just be careful, ok?” Henry heard Dean coming back into the room. “Yeah, you too.” Dean grumpily hung up. “He’s with Metatron. Angel stuff. Apparently he’ll be explaining more later.” Sam raised a brow at Dean but didn’t comment.

            “So, the tape?” Henry asked.

 

* * *

 

 

            “Did he just… cure a demon?” Sam asked, eyes wide. Henry felt about the way Sam looked.

            “Maybe,” Dean said, though he had heard the tape just as well as the others, “Could we take this hoodoo on a test drive?”

            “Um, I mean, I have the exorcism right here. All we need is the blood, consecrated ground, and a demon,” Sam said, going through a couple of papers on the table. “So, what? We summon a demon, trap it –“

            “Or,” Dean cut him off, “we use one we’ve already tagged. Do we still have dad’s old army field surgeon’s kit?” Dean had a smile on his face that Henry did not appreciate, much the same way he didn’t appreciate the sinking feeling in his stomach.

            “It’s in the trunk,” Sam said.

            “Why?” henry tried to put a firm tone along with the question, but he knew Dean’s mind was made up.

            “I think it’s time we put humpty dumpty back together again.” Dean didn’t seem to notice the death glare he was getting from Henry.

            “Are you serious about this plan?” he asked in a cool voice. Dean gave him a look like _he_ was the one who was crazy.           

            “Yeah, why?”

            “Because it is idiotic and will get both of you killed?” Henry said. Dean rolled his eyes.

            “Please, she’s not gonna kill us,” he grabbed his bottle of beer from the table and took a nonchalant sip. “We cut her up into pieces before and we’ll make sure she stays… all sliced and diced. Mostly.”

            “Then I’m coming with you,” Henry said. They weren’t keeping him out this time. Absolutely not. Dean put on his arguing face but Henry continued before anyone could say anything. “Abaddon almost killed me before. She is the reason I had to leave my son and my wife. I want to see her face when she finds out I made it. You aren’t keeping me back anymore.”

            “Henry, you need to stay here and—“

            “I swear to God, Dean, if you say ‘heal’ I’ll punch you in the face. That ‘healing’ stuff is bullshit and you know it. I’ve been better for a while and I’m coming.” Dean looked like he was about to do some punching of his own when he looked over to see Sam hiding a smile.

            “And what the hell are you smiling about, Samantha?” he demanded.

            “I told you he wasn’t going to let you keep him locked up,” Sam said. “I say he _should_ come with us. It’s his right. He’s ready.” It would have been a strong speech if he hadn’t started coughing at the end. And it wasn’t light coughing, it was wet and heavy. Dean’s eyes changed entirely and he got the tissues and gave them to Sam with a heavy hand.

            “Fine. You can come,” Dean said, “after we do one thing.”

 

* * *

 

 

            The shooting range lit up at the flick of the switch and Dean walked to the same concrete window that he had with Sam and Charlie not too long ago. He grabbed the gun from his pants and got it ready, fired it once into the head of the target at the end of the range, and then handed it to Henry.

            “You have to know how to shoot one before I’ll take you out,” Dean said. “I’m not asking for the accuracy I expect with Sam, but you have to get close.”

            The last time Henry had held a gun in his hand was the day he shot Abaddon and almost died. The thing felt as heavy in his hands now as it had that day, only now he looked at the weapon as something he had actually fired. He understood the strength at which the gun would push its way back against him when he took the shot. He felt stronger having the dangerous thing in his hands.

            Henry looked at the gun for another moment and then moved his body, trying to get into one of the stances he had seen Dean, Sam, or Charlie shoot from. He tried holding the gun in one hand and turning away from the target but his arm shook too much. He shifted to face directly forward and put both hands on the gun. It felt better, more secure. Dean was mercifully silent the whole time Henry adjusted.

            Henry took a deep breath in, out, in. He steadied his hands, looked at the target, set his shoulders, and, as he exhaled, squeezed the trigger.

            The noise was loud, even through the headphones, and the blowback shook his arms, but Henry stood strong. He was expecting it this time. He lowered the gun and both he and Dean looked down at the target. Henry had caught the shadow of the man in the left shoulder.

            Dean made a noise in the back of his throat and Henry turned to look at him. Dean was pulling a face that distinctly said, ‘hmm, not bad,’ and Henry allowed himself to agree.

            “I think we can do a little bit better,” Dean said, uncrossing his arms. “Get ready again, but this time, let the tension out of your shoulders. You’re too tight.” Henry refocused on the target. He put his hands together on the gun, put his finger lightly on the trigger, and rolled his shoulders, forcing them to relax and release. Then he started his breathing again. In, out, in, adjust, and fire on the exhale.

            And got the target dead in the heart.

            “Yeah, I thought we could do better,” Dean said. “Now let’s go do the most disgusting jigsaw puzzle of all time.”

 

* * *

 

 

            Abaddon rolled her neck and groaned, the bones crackling into place.

            “Morning sunshines,” she said, turning to look at them. Dean and Sam stood directly in front of her, Henry far off to the side.

            “Hey, it worked,” Dean said, “you both owe me a beer.”

            “And I owe you both so much,” Abaddon said, adjusting her body in the chair, “I can’t wait to tear out those pretty green eyes.” Then she paused as if she had only just realized something. “Wait, did you say ‘both’?”

            “Yeah.”

            “Yes,” came two voices at the same time. Dean’s was a grunt, Henry’s was almost elegant. He walked out of his corner a bit to stare at Abaddon fiercely. Henry was extremely proud of himself for being able to put that look of shock on the demon’s face, even for as short a time as it was.

            “Well, Henry boy, look who made it,” Abaddon said, twisting her face into a sick smile. “How have you been? Any stomach aches?”

            “Really, I’m just glad to have opposable thumbs at this point,” Henry said with a grim face.  Dean was only too happy to grin at him for the crack.

            “We figured kitty didn’t need her claws,” Abaddon glanced down at her hands, or lack thereof, and her face settled into a much more abrasive emotion that Henry couldn’t quite identify.

            “Then I’ll stump you to death, it will be swell,” Abaddon spat out at them. She shifted suddenly but didn’t move as she had intended.

            “Yeah, that’s not gonna happen either,” Sam said, “the bullet, remember?”

            “Oh, I remember little Henry baby sticking this thing in my skull,” Abaddon said. She was boiling off fury like actual heat.

            “So, you sit there like a good little bitch. We’re gonna consecrate the ground, and you’re gonna get to fessing up,” Dean said, looking far too cocky for Henry’s taste. It was like the boy didn’t realize who he was talking to. Or that he didn’t remember the running history of remarkably bad luck the Winchesters had.

            “Oh, I know this tune,” Abaddon rolled her eyes and tried to settle more comfortably. Henry listened as she explained how she ripped men apart, men he knew, people from his world. She was vicious and Henry could tell she enjoyed the details, enjoyed remembering every single thing she ever did to hurt them. They were interrupted by Sam’s phone going off. Dean gave him an annoyed glance but Sam picked up. His eyes opened wide at the greeting from the other end of the line.

            “Crowley.” Henry looked up at Sam’s tone. The tall man was angry about the caller, though Henry couldn’t quite remember the name. He may have heard it in passing but he couldn’t recall a full conversation about the man. Or whatever the thing on the other end of the phone may be.

            “Crowley? The salesman?” Abaddon asked, a comical tone to her voice. Her description didn’t really clear anything up for Henry.

            “Try the King of Hell,” Dean said. Yeah, that cleared it up a bit more. Abaddon tried to laugh it off until she looked back at Dean’s face.

            “This is a joke, right?” Henry was frustrated to be out of the loop.

            “Who the hell is Crowley?” he tried to ask quietly. Dean sighed and pointed at Abaddon.

            “Stay,” then he gestured to the other two Winchesters to follow him outside.

            “Dean, what about her?” Henry asked, gesturing. Abaddon grinned maliciously and settled into her chair in as seductive a way as was possible when you were tied down to a chair and didn’t have any hands. Somehow the move was still impressive.

            “She’ll be fine,” Dean said, following Sam out of the large warehouse. “She’s tied down and we need to take this call.”

            “Don’t rush, Henry boy,” Abaddon said, still grinning. “We have lots of time to play.” Henry fisted up his hands and pushed his nails into the palms before finally stalking out after his grandsons.

**Notes for the Chapter:**

> **Some dialogue taken directly from Supernatural writers. I make no claims to own it.** 
> 
> Chapter title from Bad Moon Rising by Credence Clearwater Revival


	5. Luck Ain't Even Lucky

**Summary for the Chapter:**

> The boys were going to have to find out about Henry reading the Supernatural books sooner or later, and telling them in order to save a life seems like the best way it could possibly go down. And let's not forget a blast from Sam's past, a bit of Crowley, and Kevin finally meeting Grandpa Winchester!

**Notes for the Chapter:**

> Well, we've come to the end of season 8. And the end of part 1 of the Henry verse. But not the end of the verse itself! Please subscribe to the whole Verse for updates on when I start posting part 2, which I have mostly written. Thanks for reading!

            “… _Denver Times_ from yesterday?” Henry walked into the phone call in the middle of Crowley speaking. The British accent was surprising to say the least. The voice in general was surprising. Henry had always assumed that the King of Hell (not that he spent a good deal of time thinking there even _was_ a King of Hell) would have a deep gravelly voice, more similar to Castiel’s. This pristine accent and careful wording didn’t seem fitting. _Although,_ he thought, _he did sound like a diplomat._ “No? Well, you should. It’s side-splitting. What the hell, I’m sexting you an address. Check it out. Then we’ll talk. Cheerio.”

            “Wait, what? Crowley?!” Sam hung up the phone angrily.

            “Got it,” Dean said from Henry’s other side. He had his phone opened up to the newspaper Crowley had indicated. Henry leaned over slightly to get a view of the headline. “Vic’s name is Tommy Collins. Tommy. Why do I know that name?” Henry swallowed. He knew that name. Well, they would have had to find out sometime, Henry supposed.

            “You saved him from a Wendigo,” Henry said, “a long time ago.” Dean looked at him in shock and Henry could see Sam pulling a similar expression in his peripheral vision.

            “How the hell do you know that?” Dean asked. Henry sighed and looked down, sticking his hands in his pockets and kicking at the dirt.

            “I read about it,” he said, attempting to be vague. He looked up and saw the moment the realization hit Dean’s face. For all Dean’s talk about hiding emotions, Henry was starting to figure out he didn’t cover them up very well after all.

            “You _read_ about it?” Dean ground out. “ _Where_ did you read about it?” Sam sighed from the left.

            “Did Charlie help you find them?” the younger Winchester asked. He was more resigned than angry, unlike Dean. Henry nodded, looking down again.     

            “I hate those damn books,” Dean said, seething. “I hate them. And why in the hell are you reading them?” Dean threw his hands up in the air. Henry let out another huge breathe of air.

            “Well, you wouldn’t tell me anything so I decided to find out for myself,” he said, finally allowing himself to look up and defend his reasons. He could be every bit as combative as Dean if he wanted to be.

            “You don’t just… dig into our lives like that!” Dean shouted. “We would have told you. Eventually.” Sam and Henry gave him identical looks of ‘that’s bullshit’ that would have been hilarious had Dean not been all worked up. “Fine! We wouldn’t have told you. But it still isn’t ok!”

            “It isn’t ok to want to know about the lives my grandsons have lived?” Henry asked. “The lives I caused to happen?” Even the air went quiet. Dean’s hands, which had still been raised in angry gesticulation, slowly lowered and Sam was giving Henry a measured look.

            “That you caused?” Sam asked, still quiet, as if yelling again would break the air around them into bits of glass. “You think you caused our lives?”

            “I know I did,” Henry said. “I left John. None of this would have gone the way it has had I not left him that night. Had I gone back when I still could.”

            “You can’t anymore?” Dean asked. _Damn,_ Henry thought, _I really didn’t want to do this yet._

            “No, I can’t,” Henry said. “I’ve… tried. Done tests. I have had a lot of time alone in the bunker. My soul was tainted by Abaddon. I can no longer use it as a power source.” Henry assumed from the look on Sam’s face that at least one Winchester had figured this out on his own. Dean looked shocked. “Besides, according to Castiel, traveling back in time would not alter what has happened now. He told me that this future is set.”

            “Well, I could have told you that,” Dean said, huffing. He couldn’t seem to have the equal measure of rage that had built up in him a few minutes earlier. “Time’s a bitch.” Henry and Sam both gave an identical small smile.

            “It isn’t your fault, Henry,” Sam said, knowing Dean wouldn’t. “Heaven has had this screwed up plan for a long time. There isn’t something you could have done.”

            “Yeah, heaven had us fucked over sideways for a long time before you made any decisions,” Dean said. He shuffled before finally forcing himself to say more. “It isn’t your fault, old man. But we’re going to talk about this book thing more later!” He pointed at Henry to emphasize his point.

            “Of course,” Henry smiled. “So what does Tommy Collins have to do with the King of Hell?”

            “Huh, I don’t know, d’ya think Crowley blew his head off?” Dean asked, “Some sort of Demon-Wendigo team-up?”

            “No clue,” Sam admitted.

            “Well, we’ll figure that one out later. As far as Crowley goes, screw him. We’ve got everything we need to put him in a permanent time-out,” Dean gestured back to the warehouse. The three Winchesters made their way back inside, carefully. The empty chair, Henry decided later, was the worst thing he had ever seen.

 

* * *

 

 

            The room had smelled like burning flesh and Henry could still feel the gross scent in his nose. He fought the urge to gag like he had when they found the body. Henry knew the Impala, which they were in once again, heading to the Ivy Motel, smelled fine. Dean would never let anything leave a scent on the car, yet somehow the smell was following Henry.

            The Ivy Motel ended up being a nice place. It was cleanly kept and didn’t smell the way Henry assumed the majority of motels Dean and Sam stayed in smelled like. The whole building was a soft robin’s egg blue and the trim looked like it was touched up regularly. There were even well-maintained hedges and a small water feature out front.

            Henry went to the door with Sam. He had figured out in the car who the next person on their list would be: Sarah Blake. Crowley was going in chronological order. First saved, first killed. It had a sick sense of poetry. Sam steeled up his shoulders and knocked on the door. It opened up fairly quickly and they were both met with a set of disbelieving eyes.

            “Sarah,” Sam greeted grimly.

            “Sam?” Sarah looked exactly as Henry had pictured her: young, beautiful, and vibrant. She looked happy, Henry thought. Though less happy now that Sam Winchester was at her door. “What’s going on?”           

            “Can we come in?” Sam asked. Sarah hesitated for the briefest of moments but Henry saw it, and assumed Sam had noticed it as well. “It’s important.”

            “Yes, right, of course,” Sarah moved out of the way and gestured them inside. She gave Henry a curious look.

            “I’m Henry,” he stuck out an awkward hand, “I’m… a friend of Sam and Dean’s.” He decided that that would have to be his introduction to people from now on, if he was to continue to go out. A friend, that was all.

            “He’s family,” Sam amended from the side, meeting Henry’s eyes evenly. It brought a smile to his face and he nodded slightly.

            “Sam, what the hell is going on?” Sarah asked. “Not that I’m not happy so see you, but I’m just curious. And mildly concerned for my safety.” Sam sighed.

            “There is something, something bad, that’s coming after you,” he said. Henry rolled his eyes.

            “Thank you, Sam, for being as vague and terrifying as possible,” he said, stepping forward. Sam gave him a look that Dean commonly referred to as bitchface #21 but Sarah smiled the tiniest bit at him. “A demon named Crowley is on his way to kill you. He is trying to kill everyone the boys have ever saved as a method of getting his way in much bigger plans. He has given us a few minutes to get here and prepare. We have about 16 minutes as of right now.” He tried to be economical with his words, something he had always excelled at in school. He knew the business side of Sarah would find it important to understand her situation quickly so she could react. Apparently he had been correct because Sarah didn’t seem to be going into hysterics.

            “A demon named Crowley is going to kill me in… 16 minutes,” Sarah looked for confirmation.

            “No,” Sam said. “No, he’s not.” A knock sounded on the door and Sam walked over to get it. Sarah looked back at Henry.

            “Family?” she inquired, tilting her head towards Sam.

            “Long story,” Henry smiled.

            “Sarah, long time,” Dean grinned as he grunted his way into the room with the number of bags in his hands. “What are you doing in Indy?”

            “I was… scouting an estate for my dad,” Sarah said. Dean made an interested noise that Henry knew meant he really wasn’t interested at all. He went over to the older Winchester and started helping to unpack the large quantities of equipment from various bags.

            “Look,” Sam said, “we’re gonna put Devil’s Traps everywhere – the windows, the door. We’ve got holy water, an exorcism ready to play on a loop, and anything that comes through that door – it’s meat. I know this is insane, but insane is kind of what we do. We’ll keep you safe.” Henry felt like the speech seemed rehearsed, like Sam had been trying to figure out what to say to Sarah all the way here. He remembered the words that he read about Dean saying years before, that Sam should have stayed and married her. He wondered what went through Sam’s head as he looked at her now.

            “Okay,” Sarah said.

            “Okay?” Dean asked, looking up. “Okay, that’s it?”

            “You’ve done it before,” she said, shrugging. Henry decided he really liked Sarah. Sam went and sat down on the bed and Sarah followed suit so Henry turned to help Dean set up the Traps and wards. They spray-painted the large symbols on every surface.

            “Dean,” Henry asked, “what do you think would have happened? If Sam had stayed with Sarah all those years ago, I mean?” Dean’s face took on a hardened quality.

            “A lot less would have happened,” Dean said. Henry took in the expression on Dean’s face and decided he would really rather not dig any more into that particular emotion. He turned back to Sarah and Sam to see them talking. Sarah fiddled with a ring on her finger, but she was smiling as she spoke to Sam.

            “She’s married,” Henry noted, quietly. Dean grunted and sprayed another sigil on the window. He threw the can back into the bag as he finished when the phone in the room started ringing. All four heads swiveled to look at it.

            “Crowley,” Dean ground out as he answered the phone. His face quickly turned from one of determined anger to fear as he took in whatever Crowley was saying on the other end. His eyes shot over to Sarah just in time for her to start choking desperately.

            “Sarah!” Sam fell down to the floor with her, “Hey! Hey! Hey! Can you hear me? Sarah?”

            “You son of a bitch!” Dean shouted. He was silent for a minute as he listened to Crowley.

            “It’s a spell!” Sam shouted, “Find the hex bag!” Henry ran to the chair in the room and started ripping apart cushions, all the time to think of any sort of counter spell. He had to know something. He had to be useful somehow. Crowley’s cold voice continued as they searched and Sarah gasped weakly from the floor.

            “Hey! Hey! Hey! You’re gonna be ok!” Sam shouted again as he wrenched the bed away from the wall and felt at the carpet.

            “Sarah?” Crowley voice echoed through the room now, “They’re your life’s work, and I’m going to rip it apart piece by piece because I can, because you can’t stop me, and because when they’re all gone, what will you have left?” Henry let out a frustrated roar as he tore the drawers from the dresser. The action broke the wood on either side of the drawer. Crowley almost chuckled over the line and Henry felt the urge to rip his throat out.

            “No! No, no, no, please, no!” Sam held Sarah’s head in his hands as she was letting out the last wisps of her air when Henry remembered. He stood straight, dropping the remains of the drawer he held and running to the duffle bad Dean had left in the middle of the room. Sarah fell lifeless and Sam let out a growl just as Henry found what he was looking for in the bag. He grabbed holy water and holy oil and dumped them both into a bowl he found in the room. Crowley was still talking.

            “You want to keep those people alive?” he said. He was almost snarling. “I want complete and utter surrender. The Tablet, the trials – you’ll give them up, or we’ll keep doing this dance. Your choice, my darlings.” The whole time he was talking, Henry was working. He grabbed a knife, sliced his hand open, and let the blood drip into the water.

           Dean and Sam were watching him like he was the crazy one. As Crowley signed off, Henry whispered and dropped a lit match into the mixture, “ _utor uti_.” The oil flared for a moment and then went out and across the room Dean dropped the phone from his hand with a sharp yelp and then held it like he had been burned. Henry ran to the object, ripped the back off the phone, and his hand emerged with the hex bag clasped tightly.

         “Match!” Henry yelled. Dean tossed him his lighter and suddenly the hex bag was ablaze. Henry looked over at Sarah and just thought over and over, _too late, too late, too late._ Sam leaned over her face and gave her a sharp burst of air and then started pounding on her chest, counting. _Too late._ And then it wasn’t. Sarah’s eyes lit up with life again as she sucked in fresh air.

          “Sarah!” Sam lifted her up. “Breathe, just breathe. You’re ok. You’re fine.” Sarah tried to breathe inwards and coughed a bit, but she kept breathing. Henry’s shoulders dropped with relief and he handed Dean’s lighter back to him. He didn’t expect the hard hand landing on his back.

         “Good job, Henry,” Dean said. His hand stayed on Henry’s shoulder, keeping him standing.

        “What happened?” Sarah coughed from the floor. She sat up with Sam’s help, her hand still over her throat like she needed the reassurance that it was going to keep her breathing this time.

        “Looks like Henry just saved your life,” Sam said, looking up at him. His eyes were wide and grateful.

        “I’m glad I’m useful for something,” he said.

        “You’re more than useful,” Dean grunted, looking down. Henry took it with a smile. It was as close as he thought he would ever get to Dean saying ‘I love you’.

        “Thank you, Henry,” Sarah said. “Thank you.” Dean looked at the phone on the ground.

        "Can’t believe the bastard hid it in the phone,” he fumed. “That dick is done for.”

        “I have a feeling he’ll be knocked down a couple of pegs when he finds out Sarah is still breathing,” Sam said, smug. Dean considered for a minute and then shook his head.

        “No,” he said, “we play this like he succeeded. Like we’re giving up the fight.” Henry looked at him.

        “You’re going to meet with him?” he asked. Dean smiled.

        “And then we cure ourselves a King of Hell.”

 

* * *

 

 

            “I can’t believe how stupid they are,” Henry grumbled. The prophet, Kevin, was looking at him strangely.

            “So… you’re their grandpa?” Kevin asked. Henry rolled his eyes.

            “Everyone always feels the need to clarify that,” he said. He paced back and forth across the floor, around the huge table covered in books that Kevin sat at. The prophet had shown up about half an hour earlier, sent by Sam and Dean while they tried their pretty much guaranteed-to-fail plan. Why on earth had he let them go?

            “Well, it isn’t exactly usual to meet anyone that Sam and Dean know, first of all,” Kevin said. “Mainly because everyone they meet ends up dead. But also, you’re a time traveler, which is not as common in the future as you may have been led to believe.” Henry stopped pacing to give Kevin a withering look.

            “No, really? I thought there were tons of time travelers nowadays, just wandering around. I can’t believe they didn’t tell me I’m the only one. I’m crushed.” Kevin laughed. “What?”

            “It’s just,” Kevin laughed again, “you are definitely related to the Winchesters.” Henry grunted and went back to pacing. “Look, gramps,” Kevin started.

            “Why do people keep calling me that?” Henry groaned.

            “Sam and Dean have saved a lot of people,” Kevin continued, ignoring Henry, “they aren’t as stupid as they seem. They’ll be fine.” They both looked up when the sound of the bunker door opening was heard.

            “Sam? Dean?” Henry called, walking around to see the door.

            “Not entirely right,” a deep voice said.

            “Cas?” Kevin came around next to Henry. Both Dean and Castiel got to the bottom of the stairs and Henry suddenly wondered if Kevin noticed how close the two stood when they were together, if the prophet knew or had guessed. It was an odd curiosity to have, but Henry couldn’t help thinking it.

            “Hello, Kevin,” Cas smiled slightly at the prophet. Dean pushed his way past the angel and the two men to put a heavy block onto the table.

            “Is this a joke?” Kevin asked, coming forward.

            “No, it’s the word of God,” Henry swallowed a laugh. The angel really could be oblivious at times. He looked over to see that Kevin hadn’t managed to contain his own laugh.

            “What?”

            “It’s a tablet, all right?” Dean said, “Translate. That’s what you do.”

            “Okay, um, it’s the Angel Tablet, which I’ve never laid eyes on in my life,” Kevin said. “You want a translation in like six hours when it took me six months and a dead mom to translate a piece of the Demon tablet?” He chuckled darkly this time and went over to retrieve a bottle of alcohol that Henry hadn’t noticed before. Kevin must have brought it in with him. “This is not what I do, it’s what I did. You told me I was out, Dean.” He took a deep drink from the glass he had poured.

            “Yeah, well—“

            “And if this is gonna be the ‘guys like us are never out’ speech, save it.” Castiel made a move like he was going to approach Kevin but he let his arms fall back after just a moment.

“Dean’s right,” he admitted. Dean look over at Cas with sad eyes that said he wasn’t as happy to be agreed with in this particular instance.

“Cas,” he reached out and put a hand on Cas’s shoulder.

“There never seems to be an out,” Cas said. “There is only ever duty.” Kevin shuffled uncomfortably.

“You can’t think that,” Henry said. Cas looked up to meet his eyes and Henry saw in their deep blue depths that he really did. The angel really didn’t think there was an end to any of this to be found. How did he keep fighting when he felt like there was nothing he could ever achieve? Cas let out a breath, which was disconcerting considering he didn’t even _need_ to breathe regularly, let alone to show a release of such _sadness._

“You are a prophet of the lord, always and forever, until the day you cease to exist and another prophet takes your place,” Castiel said. He finally seemed to register Dean’s hand on his shoulder and he stood up straighter, trying to erase the lines of emotion that had just been etched in his every body part. “Now, are you clear as to the task before you?” Kevin nodded as an answer.

The room was silent for a moment until Henry’s brain shifted back into focus and he remembered to ask, “Sam?”

            “Fine,” Dean said. “With Crowley.” Henry nodded.

            “Let’s go, Dean,” Castiel said. He turned back for a moment after he grasped Dean’s hand. “It was good to see you again, Henry.” With the sound of wings both of the men were gone.

            “Dicks,” Kevin exhaled with the smallest of laughs, like he didn’t really mean it, and Henry didn’t really think he did.

            “I can’t believe it actually worked,” Henry admitted. Kevin grunted in agreement and sat down at the table to start translating.

            “I can’t believe anything they do works, but hey, they’re still here, aren’t they?” Kevin asked. Henry considered the question for a minute.

            “Barely,” he said. “And only after a couple of tries.” But Kevin didn’t hear him. Henry shrugged and went back to Kevin’s notes about the trials, trying desperately not to over worry about whatever was happening with Sam and Crowley down at the church.

 

* * *

 

 

            Henry pretended he wasn’t trying to listen in on Kevin’s phone call with Dean, or, he _had_ been pretending until Kevin’s voice had gotten more frantic.

            “Dean?” He said into the phone, “Dean!” He looked like he was about to open his mouth again and then he stopped suddenly and sucked in his mouth like he was listening. Henry got up from the table and Kevin raised one finger in waiting. His eyes got suddenly wide and he ran back to look at his notes about the Demon Tablet and at the new Angel Tablet in their possession. Henry heard Dean’s voice yelling through the receiver but he didn’t pick up on any specific words.

            “I don’t know!” Kevin shouted, shoving papers aside fanatically. He listened for a few more beats and then stopped moving entirely.

            “What?” Henry asked, moving forward. Kevin waved him off.

            “Are you sure?” Kevin asked into the phone. He looked up at Henry uneasily and then away again. “Dean, I don’t know if… yeah. Yeah, ok. Fine.” The prophet pulled the phone from his ear and hit a button which turned the whole screen black again.

            “What did he say?” Henry asked. It had seemed too urgent on the phone and now he was worried.

            “Uh,” Kevin shifted his weight, looking down. “Dean thinks we missed something with the trials. We need to look over the notes again. ” Kevin shuffled to the table and Henry followed quickly. He sat down and grabbed a book and Kevin moved out of his sightline. “I need something from the kitchen, I’ll be right back.”

            “What are we looking for?” He asked.

            “Stuff about Sam’s trials,” Kevin said from down the hall. “Something we missed.”

            “I’m going to need something more specific, Kevin,” Henry rolled his eyes and tried to stay calm. “Something we missed like what?”

            “How to prevent Sam from dying,” Kevin said softly from somewhere to Henry’s left. Henry stilled.

            “What?”

            “Naomi visited Dean and Cas. She says the trials are going to kill Sam.” Henry put down the piece of paper he was holding and fell into his chair more heavily, trying to process. His brain finally clicked into place and he sat up again.

            “I have to go,” he said, “I have to help. Kevin? Where are you?” Henry looked around and started to stand up.

            “I’m sorry, Henry,” Kevin’s voice came from directly behind him. He felt something strong and thick hit the back of his head and then everything went black.

 

* * *

 

 

            Henry woke up to the sound of alarms blaring. Lights were going off all around him. The table, in particular, was glowing in ways it never had. He groaned as he felt the pain in the back of his head and tried to lift an arm to touch it, “tried” being the operative term.

            His hands were tied down to his chair tight, along with his ankles. He hadn’t been moved from the chair he was sitting in before Kevin knocked him out; he had just been fastened down. Kevin. Where was that little ass-wipe?

            “Kevin?” Henry called out over the sound of blaring machinery. The dark-haired prophet slid into Henry’s sightline looking visibly distressed. Well, how could he not be, with these alarms going off the way they were?

            “Henry!” Kevin called, “I’m so sorry! Dean made me promise to knock you out so you wouldn’t go after Sam!”

            “Untie me!” Henry snarled back. Kevin made a face but came forward anyway. “What the hell is going on?”

            “I have no idea,” Kevin confessed, looking utterly lost. He looked back at Henry to see him walking towards the main bunker door. “Hey, where are you going?” Henry shut the door before he had time to answer. He stalked over to the brother’s second car and got in using the key he had found in a drawer earlier to start the ignition. He scorched out of the parking space and made his way to the main road, going faster and faster, trying to ignore the burning balls of light that fell from everywhere across the sky. He figured he might have a reasonable explanation, now, for Kevin’s alarm issues.

            He pushed the gas pedal down harder. “Come on, you piece of junk, make it,” he growled, leaning forward. He knew well-enough where Sam and Dean had planned to take Crowley, he just wished it wasn’t as hard to get there. One of the balls of flame crashed down on his right, only a few feet from the car and Henry was surprised to see it seemed to be a man. He looked battered and broken, which made sense considering how far he had fallen. Henry heard his phone ring and he wrenched it out of his pocket, answering before looking at the caller ID.

            “Henry,” Kevin breathed out at the other end, “I really am sorry.”

            “Not the time, prophet boy,” Henry said and hung up. He swerved around another broken figure on the road and pushed the gas pedal hard enough he was surprised it didn’t break through the floor.

            Finally, _finally_ he was there. The last spare balls of flame fell through the sky and Henry found himself thinking how beautiful it all was. He saw the shine of the Impala and stopped abruptly, jumping out of the car without bothering to turn it off.

            Dean and Sam both sat against the car, looking up in dismay at the sky. They didn’t even hear the loud engine pull up only a few feet away from them. Henry moved forward quickly and his breath caught when he saw Sam.

            Sam was… so broken looking. As sick as he had seemed before, this was worse. His skin was a deathly gray and his eyes were sagging. He looked like he hadn’t slept in a year and hadn’t eaten in three. The noise Henry made upon seeing his grandson is what finally alerted Dean to his presence.

            “Henry!” He almost tried to get up, but then remembered how much he was supporting Sam, even in getting him to remain sitting upright. Sam’s head swiveled weakly to look at Henry too.

            “Oh, thank God,” Henry whispered, and he fell down on his knees in front of both men, “my boys.” He wrapped his arms tightly around both of them until finally the world fell silent and the last great ball of light crashed into the earth. 

**Notes for the Chapter:**

> **Again, some dialogue taken from Supernatural writers and I make no claim to it.**
> 
> Chapter title from It's My Life by Bon Jovi
> 
> Story to continue in Part 2!


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